Diethyl Ether → alpha,alpha-Diethyl-4-methyl-3-cyclohexene-1-methanol

Participants

Reaction Steps

To 9.4 g of magnesium stirred in 350 ml of diethyl ether was added 60.4 g of iodoethane over 30 minutes to produce a mildly refluxing reaction mixture. The reaction mixture was refluxed for an additional hour, and then 23 g of the methyl ester of 4-methyl-3-cyclohexene-1-carboxylic acid in 20 ml of diethyl ether was added dropwise while maintaining gentle reflux. The reaction mixture was refluxed for an additional 1/2 hour, quenched with water, and extracted with diethyl ether; the ether extract was washed with saturated NaCl solution, dried (MgSO4), and stripped to yield an oil, which upon distillation gave 23.2 g of product, b.p. 90° C. (1 mm).

Provenance & Evidence