2-Heptanol → Cyclopropanecarboxylic acid 1-methyl-hexyl ester

Reaction equation

[CH3:1][CH:2]([OH:8])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH:9]1([C:12](O)=[O:13])[CH2:11][CH2:10]1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:1][CH:2]([O:8][C:12]([CH:9]1[CH2:11][CH2:10]1)=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

Procedure

2-Heptanol (200 g, 1.72 mol) and cyclopropanecarboxylic acid (163 g, 1.90 mol) were added into toluene (500 mL), followed by p-toluenesulfonic acid (3.2 g, 0.0172 mol). The reaction mixture was heated to reflux for 6 hours, cooled to room temperature, and quenched with aqueous sodium bicarbonate (1 L). The reaction mixture was then washed with brine (0.5 L) and dried over sodium sulfate (50 g). The solvent was removed and the reaction mixture was distilled to provide the product cyclopropanecarboxylic acid 1-methyl-hexyl ester (253 g).