Hydrochloric Acid → Oleyl acetate

HRID 1156840Notes

Reaction equation

HRID 1156840 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([OH:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].N1C=CC=CC=1.Cl>C1C=CC=CC=1.CCOCC>[C:1]([O:23][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 5284499Oleyl Alcohol

Product 1

HCID 5363289Oleyl acetateYield 88.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

a solution of 2.8 g of acetyl chloride in 10 ml of dry benzene was added dropwise, with stirring, to an ice-cold solution of compound III (5.0 g) and 2.8 g of pyridine in 20 ml of dry benzene. Following addition, stirring was maintained at room temperature for 30 minutes and the mixture was then refluxed for 2 hours. The cooled mixture was diluted with 30 ml of ether and treated with sufficient cold 5% HCl to make the mixture strongly acid. The layers were separated and the aqueous layer was shaken once with 20 ml of ether; the combined organic layers were washed with three 10-ml portions of cold H2O and dried over Na2SO4. Evaporation of the solvent and distillation of the residue gave 5.1 g (85%) of compound IV as a colorless liquid boiling at 139°-143° (0.1 mm), nD25 1.4493.

Workup

  1. additionaddition
  2. temperaturethe mixture was then refluxed for 2 hours
  3. customThe layers were separated
  4. stirringthe aqueous layer was shaken once with 20 ml of ether
  5. washthe combined organic layers were washed with three 10-ml portions of cold H2O
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the solvent and distillation of the residue

Sources & evidence

ORD record
ord-eda991db75354cd9bb45762244d73dd4
Source dataset
uspto-grants-1982_06
Patent number
US04337271

Reaction notes

Loading…