Hexane → HCID 10396924, compound

29.25 g (0.174 mol) of (2E)-3-cyclohexylpropenoic acid methyl ester was dissolved in 200 ml of ether (dried over dry nap). Thereto was added 412 ml (0.383 mol) of diisobutylaluminum hydride (n-hexane solution, 0.93N) in an argon stream at -60° C. over a 15-minute period. The mixture was stirred at the same temperature for 30 minutes. n-Hexane and diethyl ether were added. The resulting mixture was washed with a saturated aqueous ammonium chloride solution, hydrochloric acid (0.2N) and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated. The concentrate was purified by silica gel column chromatography (n-hexane/ethyl acetate=19/1 to 9/1) and distillation (57.0°-58.5° C./0.40-0.42 mmHg) to obtain 20.1 g (0.143 mol) of (2E)-3-cyclohexyl-2-propen-1-ol.

1. washThe resulting mixture was washed with a saturated aqueous ammonium chloride solution, hydrochloric acid (0.2N)
2. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulfate
3. concentrationconcentrated
4. distillationThe concentrate was purified by silica gel column chromatography (n-hexane/ethyl acetate=19/1 to 9/1) and distillation (57.0°-58.5° C./0.40-0.42 mmHg)

ORD record

ord-45fbe1b53df04e7ca9b0b3bd08a7f624

Source dataset

uspto-grants-1996_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05545666