Reaction #2195474

Reaction equation

lithium diisopropylamide

cyclo-hexane ethylbenzene THF

hydrochloric acid

→

diphenyl-methanol

Yield 83.0%

diphenylmethanol

Yield 83.0%

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.ADDITIONare added to the batch
2. 2
   ExtractionThe aqueous phase is extracted with MTB ether
3. 3
   Washthe organic phase is washed with sat. sodium chloride solution
4. 4
   Dryingdried over sodium sulfate
5. 5
   Otherevaporated

Procedure

16.1 ml (120 mmol) of a 2M solution of lithium diisopropylamide in cyclo-hexane/ethylbenzene/THF are added under nitrogen and at −70° C. to a solution of 24.0 g (110 mmol) of the aromatic compound 24 in 150 ml of THF. After 1.5 hours at the low temperature, 22.1 g (100 mmol) of the aldehyde 23, dissolved in 50 ml of THF, are added to the batch. After 3 hours at −70° C., the batch is warmed to room temperature, hydrolysed and acidified using hydrochloric acid. The aqueous phase is extracted with MTB ether, and the organic phase is washed with sat. sodium chloride solution, dried over sodium sulfate, evaporated and passed through silica gel (MTB ether/n-heptane 1:10), giving 40.2 g (83%) of the diphenyl-methanol 25.

Source