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

HRID 2114160Notes

Reaction equation

HRID 2114160 reaction equation
[CH2:1]=[O:2].[OH-].[K+].[C:5]1([CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>>[OH:2][CH2:1][C:11]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

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 diethyl phenylmalonate (4.73 g), and potassium hydroxide (catalytic amount) was added thereto at 60° C. After stirring for 1.5 hours, the reaction solution was purified by chromatograophy on silica gel (ethyl acetate:hexane=1:5 to 1:2) to give the title compound (4.96 g).

Workup

  1. customat 60° C
  2. customthe reaction solution was purified by chromatograophy on silica gel (ethyl acetate:hexane=1:5 to 1:2)

Sources & evidence

ORD record
ord-a838c7e6d8ee48f28269d543c2c31135
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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