Water → Benzyl 4-formylbenzoate

HRID 2294543Notes

Reaction equation

HRID 2294543 reaction equation
[H-].[Na+].[CH:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=[O:4].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C=O)C>[CH:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:10])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 120884-Formylbenzoic acidHCID 24758Sodium hydride

Product 1

HCID 11528845Benzyl 4-formylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

1.8 g (60 mmol) of sodium hydride (80% in oil) and 50 ml of DMF are introduced under a stream of nitrogen into a round-bottomed flask. 7.5 g (50 mmol) of 4-formylbenzoic acid, dissolved in 100 ml of DMF, are added dropwise and the mixture is stirred at room temperature until gaseous evolution has ceased. A solution of 7.1 ml (60 mmol) of benzyl bromide in 50 ml of DMF is then introduced dropwise and the mixture is stirred at room temperature for four hours. The reaction medium is poured into water, the mixture is extracted with ethyl ether and the organic phase is separated after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column and eluted with a mixture of dichloromethane and hexane (50:50). After evaporation of the solvents, 10.9 g (91%) of the expected benzyl ester are collected in the form of a colorless oil.

Workup

  1. additionare added dropwise
  2. stirringthe mixture is stirred at room temperature for four hours
  3. extractionthe mixture is extracted with ethyl ether
  4. customthe organic phase is separated after settling
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a silica column
  9. washeluted with a mixture of dichloromethane and hexane (50:50)
  10. customAfter evaporation of the solvents, 10.9 g (91%) of the expected benzyl ester
  11. customare collected in the form of a colorless oil

Sources & evidence

ORD record
ord-e9ba763b3ee44b5db931bc5022d4f596
Source dataset
uspto-grants-1997_11
Patent number
US05688817

Reaction notes

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