Benzyl Bromide → o-Benzyloxyphenylacetic acid, benzyl ester

HRID 1533251Notes

Reaction equation

HRID 1533251 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)=[O:10])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11970(2-Hydroxyphenyl)acetic acid

Product 1

HCID 563142o-Benzyloxyphenylacetic acid, benzyl esterYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2-hydroxyphenyl)acetic acid (125 g) in dimethylformamide (1.9 l) was added potassium carbonate (909 g) and benzyl bromide (281 g) successively. After being stirred for 18 hours, the mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with 1N aqueous sodium hydroxide solution and brine, dried and evaporated in vacuo. Dichloromethane was added to the residue and the solution was treated with activated carbon. The mixture was filtered and evaporated to give benzyl (2-benzyloxyphenyl)acetate (132 g).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1N aqueous sodium hydroxide solution and brine
  5. customdried
  6. customevaporated in vacuo
  7. additionDichloromethane was added to the residue
  8. additionthe solution was treated with activated carbon
  9. filtrationThe mixture was filtered
  10. customevaporated

Sources & evidence

ORD record
ord-3d17054a086d4b52b171d3986bd2ad16
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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