Acetyl chloride → Ethyl 12-hydroxydodecanoate

HRID 2410624Notes

Reaction equation

HRID 2410624 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[C:16](Cl)(=O)[CH3:17]>C(O)C>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 6367Acetyl chloride2×HCID 7903412-Hydroxydodecanoic Acid

Product 1

HCID 15635900Ethyl 12-hydroxydodecanoateYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a two-neck flask with a reflux condenser under stirring and argon flux, 12-hydroxy-dodecanoic acid, (5.0 g, 23.2 mmol), ethanol (20 mL) and acetyl chloride and acetyl chloride (0.09 ml, 1.62 mmol) are added, the mixture is refluxed for 24 h. At the end the solution is concentrated with a al rotavapor under high vacuum and the raw product is purified by column chromatography on silica gel using as eluents a mixture petrol ether/ethyl acetate 5/4. 5.45 g (yield=96%) of the desired product are isolated as a pale yellow oil.

Workup

  1. temperaturethe mixture is refluxed for 24 h
  2. concentrationAt the end the solution is concentrated with a al rotavapor under high vacuum
  3. customthe raw product is purified by column chromatography on silica gel using as eluents a mixture petrol ether/ethyl acetate 5/4

Sources & evidence

ORD record
ord-e0791e5690c24e5a9832a1719fbeb62b
Source dataset
uspto-grants-2014_08
Patent number
US08816107B2

Reaction notes

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