Product Name

  • Name

    Methyl p-tert-butylphenylacetate

  • EINECS 222-602-4
  • CAS No. 3549-23-3
  • Article Data9
  • CAS DataBase
  • Density 0.987 g/cm3
  • Solubility Insoluble in water; soluble in oils
  • Melting Point
  • Formula C13H18O2
  • Boiling Point 268.2 °C at 760 mmHg
  • Molecular Weight 206.285
  • Flash Point 98.7 °C
  • Transport Information
  • Appearance Colourless oily liquid; sweet, somewhat woody-camphoraceous odour
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 3549-23-3 (Methyl p-tert-butylphenylacetate)
  • Hazard Symbols
  • Synonyms Aceticacid, (p-tert-butylphenyl)-, methyl ester (7CI,8CI);(4-tert-Butylphenyl)aceticacid methyl ester;Methyl 4-tert-butylbenzeneacetate;Methyl 4-tert-butylphenylacetate;Methyl p-tert-butylphenylacetate;
  • PSA 26.30000
  • LogP 2.69960

Synthetic route

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

4-(1,1-dimethylethyl)-benzenemethanamine
39895-55-1

4-(1,1-dimethylethyl)-benzenemethanamine

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); carbonic acid dimethyl ester; 1,4-di(diphenylphosphino)-butane at 140℃; for 24h; Inert atmosphere;74%
...Expand
methanol
67-56-1

methanol

4-tert-butylbenzyl cyanide
3288-99-1

4-tert-butylbenzyl cyanide

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid Hydrolysis; Esterification;
4-tert-butylbenzyl chloride
19692-45-6

4-tert-butylbenzyl chloride

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2O / methanol
2: p-TsOH*H2O
View Scheme
methanol
67-56-1

methanol

4-t-butylphenylacetic acid
32857-63-9

4-t-butylphenylacetic acid

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

Conditions
ConditionsYield
With sulfuric acid In methanol for 5h; Reflux;
With thionyl chloride at 60℃; for 0.5h; Cooling with ice;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

4-t-butylphenylacetic acid
32857-63-9

4-t-butylphenylacetic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; methanol; water at 23℃; for 12h;100%
With sodium hydroxide In methanol; water at 20℃;39%
With sodium hydroxide In methanol
LiOH monohydrate

LiOH monohydrate

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

4-t-butylphenylacetic acid
32857-63-9

4-t-butylphenylacetic acid

Conditions
ConditionsYield
With sulfuric acid In methanol; water99%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

2-(4-tert-butylphenyl)ethanol
5406-86-0

2-(4-tert-butylphenyl)ethanol

Conditions
ConditionsYield
With C15H29MnNO3P2(1+)*Br(1-); potassium tert-butylate; hydrogen In 1,4-dioxane at 110℃; under 22502.3 Torr; for 24h; Inert atmosphere; Autoclave;95%
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere;94%
With lithium aluminium tetrahydride In diethyl ether for 0.5h; Reduction; Heating;87%
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With iron (II) stearate; ethylenediamine In toluene at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
Stage #2: In toluene at 100℃; for 20h; Inert atmosphere; Schlenk technique;		81%
With diisobutylaluminium hydride In dichloromethane; toluene at -20 - 20℃;72%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

1-(4-(tert-butyl)benzyl)cyclopropanol
1439386-58-9

1-(4-(tert-butyl)benzyl)cyclopropanol

Conditions
ConditionsYield
With titanium(IV) isopropylate In tetrahydrofuran at 0 - 20℃; for 0.666667h; Kulinkovich Hydroxycyclopropanation; Inert atmosphere;90%
With titanium(IV) isopropylate at 0℃; for 0.5h; Kulinkovich Hydroxycyclopropanation; Inert atmosphere;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl iodide
74-88-4

methyl iodide

(+/-)-2-(4-tert-butylphenyl)propionic acid methyl ester
154320-48-6

(+/-)-2-(4-tert-butylphenyl)propionic acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 0.333333h;
Stage #2: methyl iodide In tetrahydrofuran at -70 - 20℃; for 16.0833h;		89%
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.333333h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at 0℃; for 0.5h;		86%
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: methyl iodide In tetrahydrofuran at -78℃; for 2h; Further stages.;
With lithium hexamethyldisilazane In tetrahydrofuran; hexane; water; ethyl acetate2.65 g (53%)
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

2-(4-(tert-butyl)phenyl)acetohydrazide

2-(4-(tert-butyl)phenyl)acetohydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol Reflux;88%
With hydrazine hydrate In methanol at 50℃; for 2h;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl 2-(4-(tert-butyl)phenyl)-2-oxoacetate
1034854-37-9

methyl 2-(4-(tert-butyl)phenyl)-2-oxoacetate

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With tert.-butylhydroperoxide; copper(II) oxide In water at 110℃; for 4.5h;
Stage #2: With pyridine In water at 50℃; for 4h;		85%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

4-(1,1-Dimethylethyl)phenylmethyl ketone
64321-35-3

4-(1,1-Dimethylethyl)phenylmethyl ketone

Conditions
ConditionsYield
With sodium hydride In toluene; mineral oil at 20 - 75℃; for 1.83333h; Schlenk technique; Inert atmosphere;83.5%
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With sodium hydride In toluene; mineral oil at 75℃; for 2.5h; Schlenk technique;
Stage #2: With hydrogenchloride; water; acetic acid at 130℃;		70%
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With sodium hydride In toluene at 75℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride; acetic acid In water at 130℃; for 18h; Schlenk technique; Inert atmosphere;		52%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

propargyl bromide
106-96-7

propargyl bromide

methyl 2-(4-(tert-butyl)phenyl)-2-(prop-2-yn-1-yl)pent-4-ynoate

methyl 2-(4-(tert-butyl)phenyl)-2-(prop-2-yn-1-yl)pent-4-ynoate

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: propargyl bromide In tetrahydrofuran; toluene; mineral oil at 0 - 20℃; for 16h; Inert atmosphere;		83%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

A

(E)-methyl 3-(5-(tert-butyl)-2-(2-methoxy-2-oxoethyl)phenyl)acrylate

(E)-methyl 3-(5-(tert-butyl)-2-(2-methoxy-2-oxoethyl)phenyl)acrylate

B

(2E,2'E)-dimethyl 3,3'-(5-(tert-butyl)-2-(2-methoxy-2-oxoethyl)-1,3-phenylene)diacrylate

(2E,2'E)-dimethyl 3,3'-(5-(tert-butyl)-2-(2-methoxy-2-oxoethyl)-1,3-phenylene)diacrylate

Conditions
ConditionsYield
With (S)-acetamidoalanine; palladium diacetate; silver nitrate at 80℃; for 6h; chemoselective reaction;A 81%
B 13%
...Expand
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

benzaldehyde
100-52-7

benzaldehyde

syn-methyl 2-(4-tert-butylphenyl)-3-hydroxy-3-phenylpropanoate

syn-methyl 2-(4-tert-butylphenyl)-3-hydroxy-3-phenylpropanoate

anti-methyl 2-(4-tert-butylphenyl)-3-hydroxy-3-phenylpropanoate

anti-methyl 2-(4-tert-butylphenyl)-3-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
Stage #2: benzaldehyde In dichloromethane at 20℃; for 3h; Aldol Condensation; Inert atmosphere; Overall yield = 90percent; diastereoselective reaction;		A 78%
B n/a
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane In dichloromethane at -78℃; for 2h; Inert atmosphere;
Stage #2: benzaldehyde In dichloromethane at -78℃; for 3h; Aldol Condensation; Inert atmosphere; Overall yield = 67percent; diastereoselective reaction;		A n/a
B 61%
...Expand
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

dimethyl sulfate
77-78-1

dimethyl sulfate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

methyl 3-methoxy-2-(4-tert-butylphenyl)acrylate

methyl 3-methoxy-2-(4-tert-butylphenyl)acrylate

Conditions
ConditionsYield
Stage #1: trimethyl orthoformate With titanium tetrachloride In 1,2-dichloro-ethane at 10 - 20℃; for 1h; Inert atmosphere;
Stage #2: methyl 2-(4-tert-butylphenyl)acetate In 1,2-dichloro-ethane at 0 - 20℃; for 2h; Inert atmosphere;
Stage #3: dimethyl sulfate Further stages;		77.5%
...Expand
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

d5-ethylmagnesium bromide
5780-97-2

d5-ethylmagnesium bromide

C14H16(2)H4O

C14H16(2)H4O

Conditions
ConditionsYield
With titanium(IV) isopropylate In tetrahydrofuran Inert atmosphere;76%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl 2-bromo-2-(4-(tert-butyl)phenyl)acetate
77053-60-2

methyl 2-bromo-2-(4-(tert-butyl)phenyl)acetate

Conditions
ConditionsYield
With N-Bromosuccinimide; hydrogen bromide In tetrachloromethane Heating;65%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform at 60℃; for 1h;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

4-(2-(4-(tert-butyl)phenyl)acetamido)benzoic acid

4-(2-(4-(tert-butyl)phenyl)acetamido)benzoic acid

Conditions
ConditionsYield
With trimethylaluminum In tetrahydrofuran; n-heptane at 125℃; for 0.666667h; Microwave irradiation;65%
Estragole
140-67-0

Estragole

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

C22H28O2

C22H28O2

Conditions
ConditionsYield
With titanium(IV) isopropylate; cyclohexylmagnesiumchloride In tetrahydrofuran; diethyl ether at 20℃; for 1.66667h; Kulinkovich Hydroxycyclopropanation; Inert atmosphere;61%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2,2'-(2-(4-(tert-butyl)phenyl)ethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2,2'-(2-(4-(tert-butyl)phenyl)ethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions
ConditionsYield
With ethanol; iron(II) bromide; sodium t-butanolate In toluene at 100℃; for 24.0833h; Inert atmosphere; Glovebox;60%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl 2-(4-trifluoromethylphenyl)-2-diazoacetate
1313370-94-3

methyl 2-(4-trifluoromethylphenyl)-2-diazoacetate

Conditions
ConditionsYield
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; Inert atmosphere;51%
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 12h;
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; Inert atmosphere;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde
185040-32-8

4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde

6-(4-(tert-butyl)phenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

6-(4-(tert-butyl)phenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Conditions
ConditionsYield
With potassium fluoride on basic alumina In N,N-dimethyl acetamide at 20℃; for 3h; Inert atmosphere;41%
Trifluoromethanesulfonamide
421-85-2

Trifluoromethanesulfonamide

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl 2-(4-(tert-butyl)phenyl)-2-((trifluoromethyl)sulfonamido)acetate

methyl 2-(4-(tert-butyl)phenyl)-2-((trifluoromethyl)sulfonamido)acetate

Conditions
ConditionsYield
With bis(4-bromobenzoyloxy)iodobenzene; iodine In dichloromethane at 20℃; for 14h; Schlenk technique; Inert atmosphere; Irradiation;35%
2-ethyl-1,3-dithiane
6007-23-4

2-ethyl-1,3-dithiane

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

2-[2-(4-t-butylphenyl)acetyl]-2-ethyl-1,3-dithiane
172754-37-9

2-[2-(4-t-butylphenyl)acetyl]-2-ethyl-1,3-dithiane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane 1.) -20 deg C, 1 h, 2.) -20 to 25 deg C, 17 h;
With n-butyllithium 1.) THF, hexane, -20 deg C, 1 h, 2.) THF, 25 deg C, 17 h.; Yield given. Multistep reaction;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

(4-tert-Butyl-phenyl)-(2-cyano-3-fluoro-phenyl)-acetic acid methyl ester

(4-tert-Butyl-phenyl)-(2-cyano-3-fluoro-phenyl)-acetic acid methyl ester

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran for 19h; Ambient temperature;
ethyl bromide
74-96-4

ethyl bromide

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl 2-(4-t-butylphenyl)butanoate
211314-95-3

methyl 2-(4-t-butylphenyl)butanoate

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: ethyl bromide In tetrahydrofuran at -78℃; for 2h; Further stages.;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

benzyl bromide
100-39-0

benzyl bromide

2-(4-tert-butyl-phenyl)-3-phenyl-propionic acid methyl ester
320342-75-4

2-(4-tert-butyl-phenyl)-3-phenyl-propionic acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: benzyl bromide In tetrahydrofuran at -78℃; for 2h; Further stages.;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

propyl bromide
106-94-5

propyl bromide

2-(4-tert-butyl-phenyl)-pentanoic acid methyl ester
320342-73-2

2-(4-tert-butyl-phenyl)-pentanoic acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: propyl bromide In tetrahydrofuran at -78℃; for 2h; Further stages.;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

2-(4-tert-butyl-phenyl)-4-phenyl-butyric acid methyl ester
320342-77-6

2-(4-tert-butyl-phenyl)-4-phenyl-butyric acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: 1-phenyl-2-bromoethane In tetrahydrofuran at -78℃; for 2h; Further stages.;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

(4-tert-butyl-phenyl)-acetic acid benzyl ester
1046319-72-5

(4-tert-butyl-phenyl)-acetic acid benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / methanol
2: Cs2CO3 / dimethylformamide
View Scheme

Methyl p-tert-butylphenylacetate Specification

The Benzeneacetic acid,4-(1,1-dimethylethyl)-, methyl ester, with the CAS registry number 3549-23-3, is also known as Methyl p-tert-butylphenylacetate. It belongs to the product categories of Aromatic Esters; ester Flavor; Alphabetical Listings; Flavors and Fragrances; M-N. Its EINECS number is 222-602-4. This chemical's molecular formula is C13H18O2 and formula weight is 206.28. What's more, its IUPAC name is methyl 2-(4-tert-butylphenyl)acetate.

Physical properties of Benzeneacetic acid,4-(1,1-dimethylethyl)-, methyl ester are: (1)ACD/LogP: 3.65; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 352.58; (4)ACD/KOC (pH 5.5): 2317.02; (5)#H bond acceptors: 2; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 4; (8)Polar Surface Area: 26.3 Å2; (9)Index of Refraction: 1.491; (10)Molar Refractivity: 60.59 cm3; (11)Molar Volume: 208.9 cm3; (12)Surface Tension: 31.8 dyne/cm; (13)Density: 0.987 g/cm3; (14)Flash Point: 98.7 °C; (15)Enthalpy of Vaporization: 50.63 kJ/mol; (16)Boiling Point: 268.2 °C at 760 mmHg; (17)Vapour Pressure: 0.00778 mmHg at 25°C.

Uses of Benzeneacetic acid,4-(1,1-dimethylethyl)-, methyl ester: it can be used to produce 4-tert-butyl-phenethyl alcohol which is a reduction reaction. It will need reagent LiAlH4 and solvent diethyl ether. The reaction time is 30 min by heating. The yield is about 87%.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)CC(=O)OC
(2)InChI: InChI=1S/C13H18O2/c1-13(2,3)11-7-5-10(6-8-11)9-12(14)15-4/h5-8H,9H2,1-4H3
(3)InChIKey: HXVTYMWVMVKVTF-UHFFFAOYSA-N

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