Benzyl Bromide → Benzyl 2-(3-(benzyloxy)phenyl)acetate

HRID 2114733Notes

Reaction equation

HRID 2114733 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.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=O)C>[C:19]1([CH2:18][O:1][C:2]2[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:8][C:4]3[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=3)=[O:10])[CH:5]=[CH:6][CH:7]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 15470856Benzyl 2-(3-(benzyloxy)phenyl)acetateYield 198.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxyphenyl acetic acid (5.0 g, 0.03 mol) in DMF (25 ml) was added potassium carbonate (12.4 g, 0.09 mol). The reaction was allowed to stir for twenty minutes at which time benzyl bromide (8.9 ml, 0.075 mol) was added to the flask. The reaction was allowed to stir overnight. Solvent was removed. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated to yield the title compound (9.9 g, 99% yield): ES-MS (m/z) 243 [M+H]+.

Workup

  1. additionwas added to the flask
  2. customSolvent was removed
  3. additionThe reaction was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bae80bde2a3848909adaef6ca36c8524
Source dataset
uspto-grants-2008_10
Patent number
US07435729B2

Reaction notes

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