Reaction #803670

Reaction equation

(2E)-4-cyclohexenyl-3-methylbut-2-enyl acetate

sodium hydroxide

→

(2E)-4-cyclohexenyl-3-methylbut-2-en-1-ol

Yield 93.0%

Solvents

water

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to 35° C
2. 2
   OtherThe aqueous phase was separated from the organic phase
3. 3
   WashThe organic phase was washed once with 5% w/w aqueous NaCl and twice with water

Procedure

(2E)-4-cyclohexenyl-3-methylbut-2-enyl acetate (2.08 kg, 10.0 mols, purity: 98%) sodium hydroxide (420 g, 10.5 mols) and water (8400 ml) were mixed together and heated at 90-95° C. under stirring for 10-12 h. The reaction mixture was cooled to 35° C. The aqueous phase was separated from the organic phase. The organic phase was washed once with 5% w/w aqueous NaCl and twice with water. The crude product was fractionated under reduced pressure to provide (2E)-4-cyclohexenyl-3-methylbut-2-en-1-ol (1.5 kg, yield: 93%; GC purity: 99% sum of the isomers). Reduced pressure (1 mmHg) to give 1.54 kg of (2E)-4-(cyclohex-1-en-1-yl)-3-methylbut-3-en-1-ol and (2E) isomer (yield: 93%; GC purity: 99% sum of the isomers).

Source