Product Name

  • Name

    Methyl (R)-(-)-3-hydroxybutyrate

  • EINECS 223-610-0
  • CAS No. 3976-69-0
  • Article Data174
  • CAS DataBase
  • Density 1.05 g/cm3
  • Solubility Slightly soluble in water.
  • Melting Point
  • Formula C5H10O3
  • Boiling Point 161.9 °C at 760 mmHg
  • Molecular Weight 118.133
  • Flash Point 71.7 °C
  • Transport Information
  • Appearance clear colorless liquid
  • Safety 26-36/37-24/25-23
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 3976-69-0 (Methyl (R)-(-)-3-hydroxybutyrate)
  • Hazard Symbols IrritantXi
  • Synonyms Methyl (3R)-3-hydroxybutanoate;(R)- (-)-3-Hydroxybutyric acid methyl ester;Methyl (R)-3-Hydroxybutyrate;
  • PSA 46.53000
  • LogP -0.06970

Synthetic route

(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
In diethyl ether100%
In methanol; diethyl ether at -10℃;76%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

A

(S)-3-hydroxybutyric acid methyl ester
53562-86-0

(S)-3-hydroxybutyric acid methyl ester

B

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With Ru2Cl4-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt3; hydrogen In methanol at 35℃; under 76000.1 Torr; for 48h; Title compound not separated from byproducts;A 100%
B n/a
With <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3; hydrogen In methanol at 35℃; under 76000.1 Torr; for 48h; Title compound not separated from byproducts;A n/a
B 100%
With hydrogen; Ru(BICP)Br2 In methanol at 40 - 65℃; under 750.075 - 3750.38 Torr;A n/a
B 95%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With cat; hydrogen In methanol; dichloromethane at 25℃; under 77572.2 Torr; for 48h;100%
With (R)-MeOBiphepRuBr2; hydrogen In methanol at 50℃; under 15200 Torr; for 48h;100%
With (S)-4,12-bis(diphenylphosphino)-<2.2>paracyclophane-Ru(II)bis(trifluoroacetate); hydrogen; tetra-(n-butyl)ammonium iodide In methanol; water at -5℃; under 2585.7 Torr; for 18h;100%
methanol
67-56-1

methanol

Ethyl (R)-3-hydroxybutanoate
24915-95-5

Ethyl (R)-3-hydroxybutanoate

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
scandium tris(trifluoromethanesulfonate) at 64℃; for 10h;98%
(EtO)3TiO(CH2)2OTi(OEt)3 autoclave, 1.) 160 deg C, 17 bar, 2 h; 2.) 115 deg C, 3.5 bar, 27 h;82%
tert-butyl acetoacetate
1694-31-1

tert-butyl acetoacetate

A

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

B

tert-butyl (R)-3-hydroxybutanoate
110171-06-7

tert-butyl (R)-3-hydroxybutanoate

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; [RuCl2-((R)-binap)]*NEt3 In methanol at 40℃; under 2585.7 Torr; for 8h; Kinetics; effect of acid, other substrate;A 3%
B 97%
With hydrogenchloride; hydrogen; <(R)-(BINAP)RuCl2>2*NEt3 In methanol at 40℃; under 2585.7 Torr; for 8h;A 3%
B 97%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

A

(S)-3-hydroxybutyric acid methyl ester
53562-86-0

(S)-3-hydroxybutyric acid methyl ester

B

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

C

3,3-bismethoxybutyric acid methyl ester
29267-46-7

3,3-bismethoxybutyric acid methyl ester

Conditions
ConditionsYield
With hydrogen; {RuI((R)-2,2'-bis(diphenylphospino)-1,1'-binaphthyl)(p-cymene)}I In methanol at 30℃; under 76000 Torr; for 35h; Product distribution; other: catalysts, solvents, time, pressure, temperatures;A 97%
B n/a
C 3%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

(R)-propylene oxide
15448-47-2

(R)-propylene oxide

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With 3-HYDROXYPYRIDINE; dicobalt octacarbonyl In tetrahydrofuran at 65℃; under 31028.9 Torr; for 9h;92%
(S)-3-Hydroxy-4-((R)-toluene-4-sulfinyl)-butyric acid methyl ester
142176-67-8

(S)-3-Hydroxy-4-((R)-toluene-4-sulfinyl)-butyric acid methyl ester

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With nickel90%
methanol
67-56-1

methanol

PHB/PHV biopolymer

PHB/PHV biopolymer

A

methyl (3R)-3-hydroxypentanoate
42558-50-9, 56009-31-5, 60793-22-8, 133098-13-2

methyl (3R)-3-hydroxypentanoate

B

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid In 1,2-dichloro-ethane for 48h; Heating;A 62%
B 87%
Methyl (S)-4-(p-Chlorophenylthio)-3-hydroxybutanoate
114607-86-2

Methyl (S)-4-(p-Chlorophenylthio)-3-hydroxybutanoate

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
nickel80%
methanol
67-56-1

methanol

poly(3(R)-hydroxybutyric acid)

poly(3(R)-hydroxybutyric acid)

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid In dichloromethane for 48h; Heating;78%
(2R,3R)-3-Hydroxy-2-phenylsulfanyl-butyric acid methyl ester

(2R,3R)-3-Hydroxy-2-phenylsulfanyl-butyric acid methyl ester

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With nickel In ethanol for 0.5h; Ambient temperature;75%
methanol
67-56-1

methanol

poly([R]-3-hydroxybutyrate)

poly([R]-3-hydroxybutyrate)

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid In 1,2-dichloro-ethane at 80℃; for 120h; Heating / reflux;73%
poly[(R)-3-hydroxy butyric acid]

poly[(R)-3-hydroxy butyric acid]

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid In methanol; 1,2-dichloro-ethane for 72h; depolymerization; Heating;71%
(R)-methyl 3-(dimethyl(phenyl)silyl)butanoate
166020-21-9

(R)-methyl 3-(dimethyl(phenyl)silyl)butanoate

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With peracetic acid; palladium diacetate; mercury(II) diacetate In acetic acid for 2h; Ambient temperature;43%
3-Hydroxybutyric acid
300-85-6, 625-71-8

3-Hydroxybutyric acid

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
In diethyl ether
(S)-4-Benzenesulfonyl-3-hydroxy-butyric acid methyl ester

(S)-4-Benzenesulfonyl-3-hydroxy-butyric acid methyl ester

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With Raney Ni W-4 Yield given;
(R)-3-(benzyloxy)butanoic acid methyl ester
116761-24-1

(R)-3-(benzyloxy)butanoic acid methyl ester

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In acetic acid Product distribution; Ambient temperature;
methanol
67-56-1

methanol

poly(R)-3-hydroxybutanoic acid (PHB)

poly(R)-3-hydroxybutanoic acid (PHB)

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid
methanol
67-56-1

methanol

poly-(R)-3-hydroxybuttersaeure

poly-(R)-3-hydroxybuttersaeure

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid 1.) 1,2-dichloroethane, reflux, 2 h; 2.) reflux, 48 h; Yield given. Multistep reaction;
methanol
67-56-1

methanol

Biopol (73percent (R)-3-hydroxybutanoic acid - 27percent (R)-3-hydroxyvaleric acid copolymer)

Biopol (73percent (R)-3-hydroxybutanoic acid - 27percent (R)-3-hydroxyvaleric acid copolymer)

A

methyl (3R)-3-hydroxypentanoate
42558-50-9, 56009-31-5, 60793-22-8, 133098-13-2

methyl (3R)-3-hydroxypentanoate

B

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid 1.) 1,2-dichloroethane, reflux, 1 h; 2.) 1,2-dichloroethane, reflux, 3 d; Yield given. Multistep reaction. Yields of byproduct given;
methanol
67-56-1

methanol

poly<(R)-3-hydroxybutanoic acid>

poly<(R)-3-hydroxybutanoic acid>

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid; toluene-4-sulfonic acid 1.) 1,2-dichloroethane, reflux, 34 h; 2.) 1,2-dichloroethane, reflux, 12 h; Yield given; Multistep reaction;
(+)-macrosphelide E
200335-76-8

(+)-macrosphelide E

A

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

B

methyl (E,4R,5S)-4,5-dihydroxy-2-hexenoate
63357-08-4

methyl (E,4R,5S)-4,5-dihydroxy-2-hexenoate

Conditions
ConditionsYield
Stage #1: (+)-macrosphelide E With potassium carbonate In methanol at 20℃;
Stage #2: diazomethane In diethyl ether at 20℃; for 2h; Further stages.;
methanol
67-56-1

methanol

(+)-macrosphelide E
200335-76-8

(+)-macrosphelide E

A

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

B

methyl (E,4R,5S)-4,5-dihydroxy-2-hexenoate
63357-08-4

methyl (E,4R,5S)-4,5-dihydroxy-2-hexenoate

Conditions
ConditionsYield
With sulfuric acid at 20℃; Title compound not separated from byproducts.;
3-hydroxybutyric acid methyl ester
1487-49-6

3-hydroxybutyric acid methyl ester

A

(S)-3-hydroxybutyric acid methyl ester
53562-86-0

(S)-3-hydroxybutyric acid methyl ester

B

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With air; cells of Geotrichum candidum IFO5767 In water at 30℃; for 24h; Product distribution;
With pentyl cage-coated capillary column Resolution of racemate;
With homochiral metal-organic cage [Zn3(deprotonated [3+3] macrocyclic Schiff base of trans-1,2-diaminocyclohexane and 4-tert-butyl-2,6-diformylphenol)2] coated capillary column In dichloromethane at 112℃; Resolution of racemate; enantioselective reaction;
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

isopropyl alcohol
67-63-0

isopropyl alcohol

A

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

B

3,3-diisopropoxy-butyric acid methyl ester

3,3-diisopropoxy-butyric acid methyl ester

Conditions
ConditionsYield
With hydrogen; (S)-Ru-BINAP at 60℃; under 30002.4 Torr; for 1h; Product distribution; Further Variations:; Reagents; Solvents;
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Methyl 4-(4-Chlorophenylthio)-3-oxobutanoate
114607-75-9

Methyl 4-(4-Chlorophenylthio)-3-oxobutanoate

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Candida guilliermondii
2: 80 percent / Raney nickel
View Scheme
(4S,5R)-5-Methyl-2-oxo-[1,3]dioxolane-4-carboxylic acid methyl ester

(4S,5R)-5-Methyl-2-oxo-[1,3]dioxolane-4-carboxylic acid methyl ester

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / Et3N / tetrahydrofuran / 1 h / 0 °C
2: 75 percent / Raney nickel / ethanol / 0.5 h / Ambient temperature
View Scheme
triisopropylsilyl trifluoromethanesulfonate
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

methyl 3(R)-<oxy>butanoate
126249-06-7, 122358-09-2

methyl 3(R)-<oxy>butanoate

Conditions
ConditionsYield
With 2,6-dimethylpyridine for 3h; Ambient temperature;100%
With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;95%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

methyl (R)-(-)-3-(tert-butyldimethylsilyloxy)butyrate
104524-19-8

methyl (R)-(-)-3-(tert-butyldimethylsilyloxy)butyrate

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 23℃; for 12h; Addition;100%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;100%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;100%
(R)-methoxytrifluoromethylphenylacetyl chloride
20445-33-4, 39637-99-5

(R)-methoxytrifluoromethylphenylacetyl chloride

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

methyl (3R)-3-<(S)-(-)-α-methoxy-α-(trifluoromethyl)phenylacetyl>butyrate

methyl (3R)-3-<(S)-(-)-α-methoxy-α-(trifluoromethyl)phenylacetyl>butyrate

Conditions
ConditionsYield
With pyridine In tetrachloromethane for 12h; Ambient temperature;100%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

(S)-chlorofluoroacetic acid
25197-75-5

(S)-chlorofluoroacetic acid

Methyl (3R)-3-[(2S)-2-chloro-2-fluoroacetoxy]butanoate

Methyl (3R)-3-[(2S)-2-chloro-2-fluoroacetoxy]butanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Esterification;100%
{ONOMe,Cumyl}Y[N(SiHMe2)2](THF)(Et2O)
1510836-92-6

{ONOMe,Cumyl}Y[N(SiHMe2)2](THF)(Et2O)

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

{ONOMe,Cumyl}Y((R)-OCH(CH3)CH2COOMe)

{ONOMe,Cumyl}Y((R)-OCH(CH3)CH2COOMe)

Conditions
ConditionsYield
In benzene-d6 for 0.166667h; Inert atmosphere; Glovebox;99%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

benzylamine
100-46-9

benzylamine

(R)-N-benzyl-3-hydroxybutanamide
146679-25-6

(R)-N-benzyl-3-hydroxybutanamide

Conditions
ConditionsYield
With ammonium nitrate In neat (no solvent) at 20℃; for 12h; Green chemistry;99%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

ethyl vinyl ether
109-92-2

ethyl vinyl ether

methyl (1'RS,3R)-3-(1-ethoxyethoxy)butyrate
208459-11-4

methyl (1'RS,3R)-3-(1-ethoxyethoxy)butyrate

Conditions
ConditionsYield
With trifluoroacetic acid for 12h; Ambient temperature;98%
With trifluoroacetic acid 1) 0 deg C, 22 h, 2) r.t., 3 h;94%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 24h;
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

methyl (R)-3-(p-toluenesulfonyloxy)butyrate
91366-12-0

methyl (R)-3-(p-toluenesulfonyloxy)butyrate

Conditions
ConditionsYield
With pyridine at 0℃; for 24h;98%
With pyridine; triethylamine In toluene at 0 - 20℃; Inert atmosphere;84%
With pyridine Ambient temperature;82.4%
2-Methoxyethoxymethyl chloride
3970-21-6

2-Methoxyethoxymethyl chloride

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

(R)-3-(2-Methoxy-ethoxymethoxy)-butyric acid methyl ester
160482-01-9

(R)-3-(2-Methoxy-ethoxymethoxy)-butyric acid methyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane Ambient temperature;98%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

(R)-methyl 3-(methoxy)methoxybutyrate
99274-56-3

(R)-methyl 3-(methoxy)methoxybutyrate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine97%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 42h;95%
With N-ethyl-N,N-diisopropylamine In dichloromethane
With N-ethyl-N,N-diisopropylamine In dichloromethane for 42h; Ambient temperature;
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(R)-3-(tert-Butyldiphenylsilanyloxy)butyric acid methyl ester
178246-78-1

(R)-3-(tert-Butyldiphenylsilanyloxy)butyric acid methyl ester

Conditions
ConditionsYield
Stage #1: Methyl (R)-3-hydroxybutyrate With 1H-imidazole In dichloromethane at 0℃; for 0.166667h;
Stage #2: tert-butylchlorodiphenylsilane In dichloromethane at 25℃; for 4h; Further stages.;
97%
Stage #1: Methyl (R)-3-hydroxybutyrate With 1H-imidazole In dichloromethane at 0℃; for 0.166667h; silylation;
Stage #2: tert-butylchlorodiphenylsilane In dichloromethane at 0 - 25℃; for 4h; silylation; Further stages.;
97%
With 1H-imidazole In dichloromethane at 20℃; for 4.5h;91.2%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

methyl (R)-3-tetrahydropyranyloxybutanoate
77234-51-6

methyl (R)-3-tetrahydropyranyloxybutanoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 0℃; for 2h; Etherification;96%
With toluene-4-sulfonic acid In diethyl ether for 10h; Ambient temperature;91%
With toluene-4-sulfonic acid In diethyl ether at 0 - 25℃;65%
chlorodimethyl(1,1,2-trimethylpropyl)silane
67373-56-2

chlorodimethyl(1,1,2-trimethylpropyl)silane

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

(R)-3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-butyric acid methyl ester
133260-92-1

(R)-3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-butyric acid methyl ester

Conditions
ConditionsYield
96%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

4-Methyl-benzoic acid (R)-2-methoxycarbonyl-1-methyl-ethyl ester

4-Methyl-benzoic acid (R)-2-methoxycarbonyl-1-methyl-ethyl ester

Conditions
ConditionsYield
With 4-vinylpyridine In dichloromethane at 20℃; for 6h;96%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

O-(4-methoxybenzyl)-trichloroacetimidate
89238-99-3

O-(4-methoxybenzyl)-trichloroacetimidate

(R)-methyl 3-((4-methoxybenzyl)oxy)butanoate
185030-60-8

(R)-methyl 3-((4-methoxybenzyl)oxy)butanoate

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dichloromethane at 20℃; for 36h; Etherification;95%
With camphorsulfonic acid In dichloromethane at 20℃; Inert atmosphere;94%
With camphor-10-sulfonic acid In dichloromethane at 20℃; Inert atmosphere;93.7%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

C8H15NO3

C8H15NO3

Conditions
ConditionsYield
In 2-methyltetrahydrofuran at 90℃; for 3h; Solvent; Temperature; Large scale;95%
In dichloromethane at 90℃; for 4h; Solvent; Temperature; Large scale;
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
Stage #1: Methyl (R)-3-hydroxybutyrate With potassium hydroxide In water at 0 - 20℃; for 48h; Inert atmosphere;
Stage #2: With hydrogenchloride In water pH=1; Inert atmosphere;
94%
With potassium hydroxide In water at 4℃; for 480h;91%
Stage #1: Methyl (R)-3-hydroxybutyrate With potassium hydroxide; water at 0℃; for 25.5h;
Stage #2: With hydrogenchloride; water at 5℃;
87%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

aniline
62-53-3

aniline

A

methyl (R)-3-(phenylamino)butanoate
63430-94-4

methyl (R)-3-(phenylamino)butanoate

B

(S)-phenylamino-butyric acid methyl ester
142826-92-4

(S)-phenylamino-butyric acid methyl ester

Conditions
ConditionsYield
Stage #1: Methyl (R)-3-hydroxybutyrate With trifluoromethanesulfonic acid anhydride; diisopropylamine In dichloromethane at -78℃; for 1h;
Stage #2: aniline at -78 - -40℃; for 16h;
A n/a
B 94%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

benzyl bromide
100-39-0

benzyl bromide

(R)-3-(benzyloxy)butanoic acid methyl ester
116761-24-1

(R)-3-(benzyloxy)butanoic acid methyl ester

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere;94%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

O-(4-methoxybenzyl)-trichloroacetimidate
89238-99-3

O-(4-methoxybenzyl)-trichloroacetimidate

(R)-methyl 3-((4-methoxybenzyl)oxy)butanoate

(R)-methyl 3-((4-methoxybenzyl)oxy)butanoate

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dichloromethane at 0 - 20℃;94%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

sodium (R)-3-hydroxybutyrate
13613-65-5

sodium (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With water; sodium hydroxide In methanol at 15℃; for 12h; Inert atmosphere;93.69%
With sodium hydroxide In water at 10 - 30℃; for 6h;85%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

methyl (R)-(-)-3-(tert-butyldimethylsilyloxy)butyrate
104524-19-8

methyl (R)-(-)-3-(tert-butyldimethylsilyloxy)butyrate

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 23h;92%
Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

calcium (R)-3-hydroxybutyrate

calcium (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With calcium hydroxide In water at 8℃; for 6h;91.1%

Methyl (R)-(-)-3-hydroxybutyrate Chemical Properties

Molecular Structure of Methyl (R)-(-)-3-hydroxybutyrate (CAS NO.3976-69-0):

IUPAC Name: Methyl (3R)-3-hydroxybutanoate 
Molecular Formula: C5H10O3
Molecular Weight: 118.13
EINECS: 223-610-0
XLogP3-AA: -0.2
H-Bond Donor: 1
H-Bond Acceptor: 3 
Storage temp.: 0-6 °C 
Index of Refraction: 1.42
Molar Refractivity: 28.48 cm3
Molar Volume: 112.4 cm3
Surface Tension: 33.2 dyne/cm
Density: 1.05 g/cm3
Flash Point: 71.7 °C
Enthalpy of Vaporization: 46.4 kJ/mol
Boiling Point: 161.9 °C at 760 mmHg
Vapour Pressure: 0.768 mmHg at 25 °C
Appearance: clear colorless liquid
Canonical SMILES: CC(CC(=O)OC)O
Isomeric SMILES: C[C@H](CC(=O)OC)O
InChI: InChI=1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1
InChIKey: LDLDJEAVRNAEBW-SCSAIBSYSA-N
Product Categories: Alcohols, Hydroxy Esters and Derivatives; Chiral Compounds; Building Blocks for Liquid Crystals; Chiral Building Blocks; Chiral Compounds (Building Blocks for Liquid Crystals); Functional Materials; Simple Alcohols (Chiral); Synthetic Organic Chemistry; Chiral Building Blocks; Esters; Organic Building Blocks; Chiral Alcohols

Methyl (R)-(-)-3-hydroxybutyrate Safety Profile

Safety Information of Methyl (R)-(-)-3-hydroxybutyrate (CAS NO.3976-69-0):
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37-24/25-23 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37:Wear suitable protective clothing and gloves. 
S24/25:Avoid contact with skin and eyes. 
S23:Do not breathe vapour.
WGK Germany: 3

Methyl (R)-(-)-3-hydroxybutyrate Specification

 Methyl (R)-(-)-3-hydroxybutyrate (CAS NO.3976-69-0), its Synonyms are (R)-(-)-3-Hydroxybutyric acid methyl ester ; Methyl (3R)-3-hydroxybutanoate ; Methyl R-3-hydroxybutanoate ; Methyl 3-hydroxybutanoate .

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