4-Methylbenzaldehyde → 4,4'-Dimethylbenzhydrol

Participants

Reaction Steps

To the Grignard reagent prepared from 47.2 g of p-bromotoluene and 7.2 g of magnesium in 200 ml of ether was added dropwise 30 g of p-tolualdehyde in 50 ml of ether with cooling. When the addition was complete the reaction was refluxed for 15 minutes, cooled in ice, and 40 ml of saturated NH4Cl solution was added dropwise. The reaction was filtered and the ether was removed under reduced pressure to give a yellow oil which crystallized on standing. Recrystallization from petroleum ether gave 26.1 g of nearly colorless 4,4'-dimethylbenzhydrol, m.p. 70°-71°.

Provenance & Evidence