Acetyl chloride → Ethyl 12-hydroxydodecanoate
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
Product 1
Reagents, catalysts & solvents 1
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%.