Diethyl Ether → alpha,alpha-Diethyl-4-methyl-3-cyclohexene-1-methanol
Reaction equation
[Mg].I[CH2:3][CH3:4].[CH3:5][C:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:14])=O)[CH2:8][CH:7]=1.[CH2:15](OCC)[CH3:16]>>[CH2:15]([C:12]([CH2:3][CH3:4])([CH:9]1[CH2:10][CH2:11][C:6]([CH3:5])=[CH:7][CH2:8]1)[OH:14])[CH3:16]Participants
5
Procedure
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).