Acetyl chloride → Ethyl 12-hydroxydodecanoate

HRID 2410622Notes

Reaction equation

HRID 2410622 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 chlorideHCID 7903412-Hydroxydodecanoic Acid

Product 1

HCID 15635900Ethyl 12-hydroxydodecanoateYield 833.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 mL two-neck flask with a reflux condenser and magnetic anchor, under a static flux of nitrogen, 12-hydroxy-dodecanoic acid (5.0 g, 23.2 mmol) is weighed, ethanol (20 mL) and acetyl chloride (1.62 mmol, 0.09 ml, 0.1 eq.) are added. The mixture is left stirring in reflux conditions for 24 hours. It is concentrated in the Rotavapor and in the high vacuum pump and the product is purified with column chromatography on silica gel with eluant mixture petroleum ether/ethyl acetate 5/4. 3.30 g of ethyl 12-hydroxydodecanoate are isolated as a light yellowish oil for a yield of 96%.

Workup

  1. waitThe mixture is left
  2. concentrationIt is concentrated in the Rotavapor and in the high vacuum pump
  3. customthe product is purified with column chromatography on silica gel with eluant mixture petroleum ether/ethyl acetate 5/4

Sources & evidence

ORD record
ord-9e444d66fb37404cbd6191059371cac9
Source dataset
uspto-grants-2014_08
Patent number
US08816107B2

Reaction notes

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