Reaction #803671

Reaction equation

NaOCl

NaBr

NaHCO3

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

→

(2E)-4-cyclohexenyl-3-methylbut-2-enal

Yield 66.0%

Solvents

toluene

water

Conditions

Workup

1. 1
   OtherThe aqueous phase was removed
2. 2
   Washorganic phase was washed with a solution of NaHCO3
3. 3
   OtherThe organic phase thus obtained
4. 4
   Concentrationwas concentrated
5. 5
   workup.DISTILLATIONcrude product purified by fractional distillation

Procedure

NaBr (0.6 g, 0.006 mol) and NaHCO3 (6.4 g, 0.076 mol) were mixed together with water (60 ml), toluene (250 g) and (2E)-4-cyclohexenyl-3-methylbut-2-en-1-ol (96 g (0.573 mol, purity: 99% sum of the isomers) at room temperature with continuous stirring. NaOCl (13% w/w aqueous 426.8 g, 0.745 mol) was added to the reaction mass over 2 h. Stirring was continued for another 1 h. The aqueous phase was removed, organic phase was washed with a solution of NaHCO3 and then with water. The organic phase thus obtained was concentrated and crude product purified by fractional distillation to provide (2E)-4-cyclohexenyl-3-methylbut-2-enal (62.6 g, yield: 66%, GC purity: 95% sum of the isomers).

Source