1-Butanol → 2-​Octen-​1-​ol

Temperature

0 °C

A hexane solution of n-butyllithium (2.1 mmol) was cooled at 0° C. under the argon atmosphere. A hexane solution of n-butanol (75.9 mg; 1.0 mmol) was added dropwise thereto and stirred. To the resulting solution, there was further added dropwise a hexane solution of 3,4-epoxy-butene-1 (70.0 mg; 1 mmol), and after the addition was completed, the resulting mixture was cooled at 0° C. for 1 hour and at room temperature for 30 minutes, followed by the usual work up. Removal of the solvent and distillation of the residue gave 63 mg of 2-octen-1-ol (yield, 49%). After acetylation of the thus obtained product, gas chromatographic analysis (PEG 20M, 4 m) was effected at a temperature of 130° C. The retention times of Z-isomer and E-isomer were respectively 13.7 minutes and 14.7 minutes, and the Z/E ratio was 89.1/10.9.

1. additionafter the addition
2. customRemoval of the solvent and distillation of the residue

ORD record

ord-8a2f5c81f36d484090b38e2a2786b4ee

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05004843