Formaldehyde → Diethyl 2-(hydroxymethyl)-2-phenylmalonate

HRID 494382Notes

Reaction equation

HRID 494382 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

Reactant 3

HCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 66514Diethyl phenylmalonate

Product 1

HCID 22236963Diethyl 2-(hydroxymethyl)-2-phenylmalonateYield 93%

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

  1. customat 60° C
  2. customthe reaction mixture was purified by column chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-a39b44c0a38b4084a5c0698c9832f5b1
Source dataset
uspto-grants-2009_05
Patent number
US07538140B2

Reaction notes

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