Conditions | Yield |
---|---|
Stage #1: 12-oxooctadecanoic acid With sodium tetrahydroborate In ethanol at 20℃; for 1.5h; Stage #2: With acetic acid In ethanol | 96% |
With sodium tetrahydroborate; ethanol at 20℃; for 1.5h; | 96% |
With sodium hydroxide; hydrogen; nickel In ethanol at 160℃; under 750.06 Torr; for 6h; | 94% |
(reduction); |
ethyl 12-hydroxystearate
12-Hydroxystearic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 6h; Heating; | 96% |
methyl 12-hydroxyoctadecanoate
12-Hydroxystearic acid
Conditions | Yield |
---|---|
With potassium hydroxide | |
With potassium hydroxide | |
With potassium hydroxide In methanol at 80℃; for 5h; Yield given; | |
With potassium hydroxide |
Conditions | Yield |
---|---|
With Pt(2+)*HO(1-) Hydrogenation.in alkoh.Loesung; | |
Reaktion des Glycerids bei der katalytischen Hydrierung.Hydrogenation; | |
Multi-step reaction with 2 steps 2: hydrogen bromide / Reduktion des Additionsprodukts mit Zink oder Zinn und Salzsaeure und nachherige Behandlung mit Kalilauge View Scheme |
12-Hydroxystearic acid
Conditions | Yield |
---|---|
With acetyl chloride man hydriert das Acetat des Ricinolsaeure-methylesters bei Gegenwart von Platinmohr in Eisessig und kocht das Reaktionsprodukt mit alkoh. Kalilauge; |
12-acetoxy-octadec-9-enoic acid
12-Hydroxystearic acid
Conditions | Yield |
---|---|
With hydrogen bromide Reduktion des Additionsprodukts mit Zink oder Zinn und Salzsaeure und nachherige Behandlung mit Kalilauge; |
methyl ricinoleate
12-Hydroxystearic acid
Conditions | Yield |
---|---|
With diethyl ether; hydrogen; platinum man verseift den entstehenden Methylester mit alkoholischer Kalilauge; | |
Multi-step reaction with 2 steps 1: H2 / Raney-Ni 2: aq. KOH View Scheme |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 2h; Heating; |
12-hydroxystearonitrile
12-Hydroxystearic acid
Conditions | Yield |
---|---|
With potassium hydroxide; water In ethanol for 40h; heating; | 8.94 g |
12-Hydroxystearic acid
Conditions | Yield |
---|---|
With hydrogen; nickel In sodium hydroxide at 120℃; under 14710.2 Torr; | 6.6 g |
12-Hydroxystearic acid
Conditions | Yield |
---|---|
With acetic acid-sulphuric acid nachfolgende Hydrierung; |
Conditions | Yield |
---|---|
Electrolysis.anschliessendes Hydrolyse mit Hilfe von Alkalilauge; |
12-acetoxy-octadec-9-enoic acid
hydrogen bromide
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Reduktion und nachfolgende Verseifung; acetate of/the/ ricinolic acid; |
Conditions | Yield |
---|---|
an der Luft; |
12-Hydroxystearic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
11-cyanoundecanoyl chloride
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: CH2Cl2 / 4 h / 20 °C 2: aq. sodium hydroxide / ethanol / 20 h / Heating 3: 94 percent / H2, NaOH / Raney nickel / aq. ethanol / 6 h / 160 °C / 750.06 Torr View Scheme | |
Multi-step reaction with 3 steps 1: 89 percent / CH2Cl2 / 1) -30 gradC, 1 h; 2) 20 gradC, 12 h 2: aq. sodium hydroxide / ethanol / 20 h / Heating 3: 94 percent / H2, NaOH / Raney nickel / aq. ethanol / 6 h / 160 °C / 750.06 Torr View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / SOCl2 / benzene / 4 h / 60 °C 2: CH2Cl2 / 4 h / 20 °C 3: aq. sodium hydroxide / ethanol / 20 h / Heating 4: 94 percent / H2, NaOH / Raney nickel / aq. ethanol / 6 h / 160 °C / 750.06 Torr View Scheme | |
Multi-step reaction with 4 steps 1: 95 percent / SOCl2 / benzene / 4 h / 60 °C 2: 89 percent / CH2Cl2 / 1) -30 gradC, 1 h; 2) 20 gradC, 12 h 3: aq. sodium hydroxide / ethanol / 20 h / Heating 4: 94 percent / H2, NaOH / Raney nickel / aq. ethanol / 6 h / 160 °C / 750.06 Torr View Scheme |
12-oxo-octadecanenitrile
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. sodium hydroxide / ethanol / 20 h / Heating 2: 94 percent / H2, NaOH / Raney nickel / aq. ethanol / 6 h / 160 °C / 750.06 Torr View Scheme |
1,12-dodecadicarboxylic acid monoethyl ester
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 93 percent / SOCl2 / 4 h / Heating 2: 1) Mg / 1) THF, -78 gradC, 1.5 h; 2) raised to 20 gradC 3: 91 percent / H2 / Raney nickel / ethanol / 15 h / 150 °C 4: 96 percent / NaOH / aq. ethanol / 6 h / Heating View Scheme |
monoethyl ester of dodecanedioic acid chloride
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1) Mg / 1) THF, -78 gradC, 1.5 h; 2) raised to 20 gradC 2: 91 percent / H2 / Raney nickel / ethanol / 15 h / 150 °C 3: 96 percent / NaOH / aq. ethanol / 6 h / Heating View Scheme |
ethyl 12-oxo-octadecanoate
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91 percent / H2 / Raney nickel / ethanol / 15 h / 150 °C 2: 96 percent / NaOH / aq. ethanol / 6 h / Heating View Scheme |
12-oxododecanenitrile
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 10 g / diethyl ether / 2 h / 20 °C 2: 8.94 g / KOH, H2O / ethanol / 40 h / heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 93 percent / Cu/Cr/Zn / 5 h / 250 - 280 °C 2: 71 percent / tert-butyl peroxide / 3 h / 150 - 160 °C 3: 68 percent / peracetic acid, permaleic acid / CH2Cl2 / 24 h / Heating 4: KOH / ethanol / 2 h / Heating View Scheme |
2-hexylcyclododecanone
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 68 percent / peracetic acid, permaleic acid / CH2Cl2 / 24 h / Heating 2: KOH / ethanol / 2 h / Heating View Scheme |
n-hexylmagnesium chloride
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 10 g / diethyl ether / 2 h / 20 °C 2: 8.94 g / KOH, H2O / ethanol / 40 h / heating View Scheme | |
Multi-step reaction with 3 steps 1: diethyl ether / 2 h / 20 °C 2: 8 g / KOH, H2O / ethanol / 40 h / heating 3: 6.6 g / H2 / Raney nickel / aq. NaOH / 120 °C / 14710.2 Torr View Scheme |
12-oxo-4,8-dodecadienenitrile
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: diethyl ether / 2 h / 20 °C 2: 8 g / KOH, H2O / ethanol / 40 h / heating 3: 6.6 g / H2 / Raney nickel / aq. NaOH / 120 °C / 14710.2 Torr View Scheme |
2-methoxycyclododecadienone oxime
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: PCl5 / diethyl ether / 2 h / 20 °C 2: diethyl ether / 2 h / 20 °C 3: 8 g / KOH, H2O / ethanol / 40 h / heating 4: 6.6 g / H2 / Raney nickel / aq. NaOH / 120 °C / 14710.2 Torr View Scheme |
12-Hydroxystearic acid
12-iodostearic acid
Conditions | Yield |
---|---|
With phosphorus; hydrogen iodide for 18h; Heating; | 100% |
methanol
12-Hydroxystearic acid
methyl 12-hydroxyoctadecanoate
Conditions | Yield |
---|---|
With hydroxy-substituted sulfonic acid-functionalized silica (HO-SAS) In tetrahydrofuran at 110℃; Fischer-Speier Esterification; Flow reactor; | 99% |
With hydrogenchloride at 40 - 50℃; for 3h; | 27.9% |
With hydrogenchloride Heating; Yield given; | |
With boron trifluoride Esterification; Heating; | |
With sulfuric acid for 16h; Heating; |
Conditions | Yield |
---|---|
With pyridine In tert-butyl methyl ether at 50℃; for 19h; | 97% |
Conditions | Yield |
---|---|
With sulfuric acid at 78℃; for 20h; Heating / reflux; | 96% |
With hydrogenchloride |
12-Hydroxystearic acid
butan-1-ol
12-hydroxy-octadecanoic acid butyl ester
Conditions | Yield |
---|---|
iodine for 15h; Heating; | 95% |
12-Hydroxystearic acid
Conditions | Yield |
---|---|
Product distribution / selectivity; | 95% |
With lithium hydroxide In water Product distribution / selectivity; | 91% |
With lithium hydroxide In water at 90℃; for 1.75h; Purification / work up; |
Conditions | Yield |
---|---|
With triethylamine; 3-diphenyloxyphosphinyl-2-oxazolidinone In acetonitrile for 1h; Ambient temperature; | 93% |
With pyridine; O-phenyl phosphorodichloridate In 1,2-dimethoxyethane for 16h; Ambient temperature; | 78% |
(i) 2-fluoro-1-methyl-pyridinium toluene-4-sulfonate, Et3N, (ii) /BRN= 506523/, Et3N; Multistep reaction; |
12-Hydroxystearic acid
A
3,16-dihexyl-2,15-dioxacyclohexacosane-1,14-dione
B
12-hydroxyoctadecanoic acid lactone
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; TiCl2(OTf)2; 4-(trifluoromethyl)benzoic anhydride In dichloromethane Heating; | A 6% B 91% |
With chloro-trimethyl-silane; TiCl2(OTf)2; 4-(trifluoromethyl)benzoic anhydride In dichloromethane at 50℃; for 5h; | A 3% B 91% |
With dmap; 2-methyl-6-nitrobenzoic anhydride In dichloromethane at 20℃; for 15h; | A 1% B 86% |
Conditions | Yield |
---|---|
distannoxane (X=Cl) In decane for 24h; Heating; | A 90% B 19% |
12-Hydroxystearic acid
12-bromostearic acid
Conditions | Yield |
---|---|
With hydrogen bromide for 18h; Heating; | 90% |
With 1H-imidazole; carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 21h; | 71% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; | 90% |
12-Hydroxystearic acid
Diphenyl 2-oxo-3-oxazolinylphosphonate
3-(12-hydroxystearoyl)-2-oxazolone
Conditions | Yield |
---|---|
With triethylamine In acetonitrile Ambient temperature; | 88% |
With triethylamine In acetonitrile | 88% |
Conditions | Yield |
---|---|
With dmap; 2-methyl-6-nitrobenzoic anhydride In dichloromethane at 20℃; for 1h; | 86% |
Stage #1: 12-Hydroxystearic acid With 2,6-dichloro-4-(perfluorohexyl)benzoyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; for 1h; Yamaguchi Lactonization; Stage #2: With dmap In tetrahydrofuran; toluene for 3h; Reagent/catalyst; Yamaguchi Lactonization; Reflux; | 86% |
With 1,3,5-trichloro-2,4,6-triazine; triethylamine In acetone for 6h; Ambient temperature; | 70% |
Conditions | Yield |
---|---|
With triethylamine; 3-diphenyloxyphosphinyl-2-oxazolidinone In N,N-dimethyl-formamide for 0.5h; Ambient temperature; | 86% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; | 85% |
12-Hydroxystearic acid
1-amino-3-(dimethylamino)propane
γ-12-Hydroxystearamidopropyl-dimethylamine
Conditions | Yield |
---|---|
at 160℃; for 12h; | 85% |
vinyl acetate
12-Hydroxystearic acid
12-hydroxyoctadecanoic acid vinyl ester
Conditions | Yield |
---|---|
With potassium hydroxide; palladium diacetate for 24h; Ambient temperature; | 83% |
12-Hydroxystearic acid
3,16-dihexyl-2,15-dioxacyclohexacosane-1,14-dione
Conditions | Yield |
---|---|
With hydrogenchloride for 18h; Heating; | 83% |
Conditions | Yield |
---|---|
With oxalyl dichloride; triethylamine In dichloromethane at -60 - 20℃; for 0.5h; Swern oxidation; | 80% |
Conditions | Yield |
---|---|
With oxidized hydroxyethyl cellulose aminated with dodecylamine In glycerol at 90℃; | 80% |
Conditions | Yield |
---|---|
With mesoporous silica HMS2-SO3H; cetyltritylammonium bromide for 6h; Product distribution; Further Variations:; Reagents; reaction times; | 77% |
With phenylboronic acid In hexane Enzymatic reaction; |
Conditions | Yield |
---|---|
Stage #1: 12-Hydroxystearic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 2,4-(3,4-dimethylbenzylidene)-D-glucose hydrazide In N,N-dimethyl-formamide at 20℃; for 5h; | 74.8% |
12-Hydroxystearic acid
2-chloro-1-methyl-pyridinium iodide
12-hydroxyoctadecanoic acid lactone
Conditions | Yield |
---|---|
With triethylamine In acetonitrile | 66% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at -10 - 20℃; for 20h; Inert atmosphere; | 66% |
With lithium aluminium tetrahydride Inert atmosphere; |
12-Hydroxystearic acid
docosanoic acid 2-hexadecanoyloxy-3-hydroxy-propyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Esterification; | 64% |
Conditions | Yield |
---|---|
With manganese; (1,2-dimethoxyethane)dichloronickel(II); 6,6'-dimethyl-4,4'-diphenyl-2,2'-bipyridine In methanol; N,N-dimethyl-formamide at 0℃; under 760.051 Torr; | 59% |
Conditions | Yield |
---|---|
With dmap; dacarbazine; 4-N,N-dimethylaminopyridine trifluoroacetate In dichloromethane at 20℃; for 4h; Esterification; | 52% |
12-Hydroxystearic acid
N1,N3-bis(hydroxymethyl)-5-fluorouracil
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide; dmap In N,N-dimethyl-formamide; acetonitrile room temp. -- 40 deg C, 24 h; | 49% |
Reported in EPA TSCA Inventory.
The IUPAC name of this chemical is 12-Hydroxystearicacid. With the CAS registry number 106-14-9 and EINECS registry number 203-366-1, it is also named as octadecanoic acid,12-hydroxy-. In addition, the molecular formula is C18H36O3. It is a kind of white powder and can be used in textile lubricants, paint and metal processing oil.
Physical properties about this chemical are: (1)ACD/LogP: 6.03; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.23; (4)ACD/LogD (pH 7.4): 3.44; (5)ACD/BCF (pH 5.5): 3580.7; (6)ACD/BCF (pH 7.4): 57.44; (7)ACD/KOC (pH 5.5): 7231.41; (8)ACD/KOC (pH 7.4): 116.01; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 17; (12)Polar Surface Area: 35.53 Å2; (13)Index of Refraction: 1.468; (14)Molar Refractivity: 88.49 cm3; (15)Molar Volume: 318.1 cm3; (16)Polarizability: 35.08 ×10-24cm3; (17)Surface Tension: 36.9 dyne/cm; (18)Density: 0.944 g/cm3; (19)Flash Point: 231.8 °C; (20)Enthalpy of Vaporization: 79.96 kJ/mol; (21)Boiling Point: 436.3 °C at 760 mmHg; (22)Vapour Pressure: 1.92E-09 mmHg at 25°C.
Preparation of 12-Hydroxystearicacid: it can be prepared by 12-hydroxy-octadecanoic acid ethyl ester. This reaction will need reagent NaOH and solvent aq. ethanol. The reaction time is 6 hours by heating. The yield is about 96%.
Uses of 12-Hydroxystearicacid: it can react with benzenethiol to get 12-Hydroxy-octadecanoyl-phenyl-thioether. This reaction will need reagents diphenyl 2-oxo-3-oxazolinylphosphonate and triethylamine, and solvent acetonitrile. The reaction time is 1 hour with ambient temperature. The yield is about 93%.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CCCCCCCCCCC(O)CCCCCC
(2)InChI: InChI=1/C18H36O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21)
(3)InChIKey: ULQISTXYYBZJSJ-UHFFFAOYAY
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