Réaction #57396

Équation de réaction

2-methyl-3-(4-methylphenyl)-2-propen-1-ol

dimethylformamide

sodium carbonate

thionyl chloride

→

title compound

Rendement 87.3%

1-(3-chloro-2-methyl-1-propenyl)-4-methylbenzene

Rendement 87.3%

Solvants

toluene

toluene

Water

toluene

Conditions de réaction

Traitement

1. 1
   Températureunder ice-cooling
2. 2
   Lavagewashed successively with 5% sodium hydrogencarbonate and 5% brine
3. 3
   workup.DISTILLATIONThe solvent was distilled off

Mode opératoire

To a solution of 2-methyl-3-(4-methylphenyl)-2-propen-1-ol (750 g) in toluene (2367 ml) was added dimethylformamide (29.6 ml). To the solution was added dropwise thionyl chloride (431.1 ml) at 20° C. or below and the solution was stirred at 12 to 15° C. for 1.5 hr. Water was then added thereto under ice-cooling. The toluene layer was fractionated and a 10% aqueous solution of sodium carbonate was added thereto to adjust the pH to 5. The toluene layer was fractionated again, washed successively with 5% sodium hydrogencarbonate and 5% brine. The solvent was distilled off to give the title compound as an oil (776.8 g, yield 87.3%).

Source