Water → Allyl 4-formylbenzoate

HRID 2294545Notes

Reaction equation

HRID 2294545 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

3.3 g (0.11 mol) of sodium hydride (80% in oil) and 100 ml of DMF are introduced under a stream of nitrogen into a round-bottomed flask. 15 g (0.1 mol) of 4-formylbenzoic acid, dissolved in 200 ml of DMF are added dropwise and the mixture is stirred at room temperature until gaseous evolution has ceased. 9.5 ml (0.11 mol) of allyl bromide are then introduced 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, then dried over magnesium sulphate and evaporated. 19 g (100%) of allyl ester are collected in the form of a slightly yellow 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. custom19 g (100%) of allyl ester are collected in the form of a slightly yellow oil

Sources & evidence

ORD record
ord-3e98e8db1e5b4959949376dc639cae8c
Source dataset
uspto-grants-1997_11
Patent number
US05688817

Reaction notes

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