4-Methylbenzaldehyde → Di(tert-butyl) hydroxy(4-methylphenyl)methylphosphonate

Participants

Reaction Conditions

Reaction Steps

To a solution of di-tert-butylphosphite (30 g) in THF (700 mL) cooled at −78° C. was added dropwise a solution of LiN(TMS)2 (165 mL, 1M in THF). After stirring for 30 min at −78° C., a solution of 4-tolualdehyde (18 mL in 100 mL of THF) was added. The reaction mixture was stirred for 30 min at −78° C. and 2 h at 0° C., and then quenched with 400 mL of 50% saturated aqueous NH4Cl solution. The mixture was extracted with 1 L of 2:1 hexane/EtOAc and the extract was dried over Na2SO4. After concentration and swishing from hexane, 32 g of the title compound was obtained as a white solid.

Provenance & Evidence