Formaldehyde → Diethyl 2-(hydroxymethyl)-2-phenylmalonate
Reaction equation
[CH2:1]=[O:2].[OH-].[K+].[CH2:5]([O:7][C:8](=[O:21])[CH:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:6]>>[CH2:13]([O:12][C:10](=[O:11])[C:9]([CH2:1][OH:2])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([O:7][CH2:5][CH3:6])=[O:21])[CH3:14]Participants
4
Procedure
Paraformaldehyde (720 mg) was suspended in phenylmalonic acid diethyl ester (4.73 g), and a catalytic amount of potassium hydroxide was added thereto at 60° C. After stirring for 1.5 hours, the reaction mixture was purified by column chromatography on silica gel with ethyl acetate:hexane=1:5 to 1:2 to give the title compound (4.96 g).
Workup
- customat 60° C
- custom