Water → Allyl 4-formylbenzoate

HRID 2268212Notes

Reaction equation

HRID 2268212 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)[CH:15]=[CH2:16].O>CN(C=O)C>[CH:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH2:16][CH:15]=[CH2:14])=[O:10])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 120884-Formylbenzoic acidHCID 24758Sodium hydride

Product 1

HCID 18381245Allyl 4-formylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3.8 g (12 mmol) of sodium hydride (80% in oil) and 100 ml of DMF are introduced into a three-necked flask under a stream of nitrogen. A solution of 15 g (10 mmol) of 4-formylbenzoic acid in 100 ml of DMF is added dropwise and the mixture is stirred until the evolution of gas has ceased. 10 ml (12 mmol) of allyl bromide are then added and the mixture is stirred at room temperature for four hours. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. 17.2 g (90%) of the expected allyl ester are collected in the form of a yellow oil.

Workup

  1. stirringthe mixture is stirred at room temperature for four hours
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom17.2 g (90%) of the expected allyl ester are collected in the form of a yellow oil

Sources & evidence

ORD record
ord-1674d0cdf5134149b582b907c3e60340
Source dataset
uspto-grants-2001_12
Patent number
US06326510B1

Reaction notes

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