Allyl bromide → Benzoic acid, 2-(2-propenyloxy)-, ethyl ester

HRID 619146Notes

Reaction equation

HRID 619146 reaction equation
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CN(C=O)C>[CH2:21]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH2:11][CH3:12])=[O:9])[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8365Ethyl SalicylateHCID 11430Potassium Carbonate

Product 1

HCID 10398065Benzoic acid, 2-(2-propenyloxy)-, ethyl esterYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl salicylate (100 g, 0.602 mol) in DMF (400 ml) was added K2CO3 (150 g), followed by the dropwise addition of allyl bromide (87.5 g, 0.723 mol). The reaction mixture was then heated on a steam bath for 2 hours, the K2CO3 was removed by filtration and the reaction mixture was poured into water and extracted with ethyl acetate (3×300 ml). The organic layer was washed with brine, and dried over MgSO4, and the solvent was removed to afford 122 g (98%) of ethyl 2-(2-propenyloxy)benzoate.

Workup

  1. temperatureThe reaction mixture was then heated on a steam bath for 2 hours
  2. customthe K2CO3 was removed by filtration
  3. additionthe reaction mixture was poured into water
  4. extractionextracted with ethyl acetate (3×300 ml)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-bbc4ee2b7f334308b9315ca632cfd675
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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