Water → HCID 21474599, compound

HRID 1756435Notes

Reaction equation

HRID 1756435 reaction equation
[H-].[Na+].[C:3]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[CH2:15](Br)[CH:16]=[CH2:17].O>CN(C=O)C>[C:3]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH2:17][CH:16]=[CH2:15])=[O:11])=[CH:8][CH:7]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 114704-Acetylbenzoic AcidHCID 24758Sodium hydride

Product 1

HCID 21474599HCID 21474599, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.65 g (55 mmol) of sodium hydride (80% in oil ) and 50 ml of DMF are introduced under a stream of nitrogen into a round-bottomed flask. 8.2 g (50 mmol) of 4-acetylbenzoic acid, dissolved in 100 ml of DMF, are added dropwise and the mixture is stirred at room temperature until gaseous evolution has ceased. 4.6 ml (55 mmol) of allyl bromide are then introduced and the mixture is stirred at room temperature for 24 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. The residue obtained is purified by chromatography on a silica column, eluting with a mixture of dichloromethane and hexane (80:20). After evaporation of the solvents, 7.2 g (71 % ) of allyl ester are collected in the form of a colorless oil.

Workup

  1. additionare added dropwise
  2. stirringthe mixture is stirred at room temperature for 24 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. washeluting with a mixture of dichloromethane and hexane (80:20)
  10. customAfter evaporation of the solvents, 7.2 g (71 % ) of allyl ester
  11. customare collected in the form of a colorless oil

Sources & evidence

ORD record
ord-65f243a23ecb4f42ba133e0ed3b3d88a
Source dataset
uspto-grants-1995_08
Patent number
US05439925

Reaction notes

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