1-Butanol → 2-Methyl-2-octen-1-ol

Participants

Reaction Steps

A hexane solution of n-butyllithium (2.1 mmol) was cooled to 0° C. under an argon atmosphere, and a hexane solution of n-butanol (74 mg; 1.0 mmol) was added dropwise thereto and stirred. A hexane solution of 3-methyl-3,4-epoxybutene-1 (84.4 mg; 1.0 mmol) was further added thereto, and after the addition was completed, the reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 1 hour, followed by the usual work up. Removal of the solvent and distillation of the residue gave 104 mg of 2-methyl-2-octen-1-ol (yield, 73%). NMR spectrum and gas chromatographic analysis (Golay column, PEG 20M, 45 m, at 140° ) showed that the resulting product contained none of 3-methyl-1-octen-4-ol, 2-methyl-2-vinylhexen-1-ol, 3-methyl-1-octen-3-ol, etc. The Z/E ratio of 2-methyl-2-octen-1-ol was 97.2/2.8.

Provenance & Evidence