4-Nitrobenzaldehyde → HCID 10661075, compound
Reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[PH2:12]([O:14][CH2:15][CH3:16])=[O:13].C(N(CC)CC)C.C([O:27][CH2:28][CH3:29])(=O)C>>[OH:9][CH:8]([P:12](=[O:13])([O:27][CH2:28][CH3:29])[O:14][CH2:15][CH3:16])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1Participants
5
Procedure
To a mixture of 4-nitrobenzaldehyde (8.56 g) and ethyl hypophosphite (7.81 g) was gradually added triethylamine (1.5 mL). After stirring for 1 hr., the reaction mixture was diluted with ethyl acetate and washed successively with 1N hydrochloric acid and water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, and diethyl α-hydroxy-4-nitrobenzylphosphonate was obtained as crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). Recrystallization from ethyl acetate-hexane gave yellow prism crystals (4.62 g, yield 28%). melting point: 94–95° C.