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

HRID 1063814Notes

Reaction equation

HRID 1063814 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.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:12]([O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=2)[CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

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

Product 1

HCID 15470856Benzyl 2-(3-(benzyloxy)phenyl)acetateYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxy-phenyl-acetic acid (15.3 g, 101 mmol), benzyl bromide (36.2 g, 202 mmol) and potassium carbonate (29.2 g, 202 mmol) were suspended in dimethylformamide (300 ml) and the reaction was heated to reflux under nitrogen for 44 hours. The reaction mixture was cooled, filtered and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 ml) and water (200 ml), and the aqueous phase was extracted with ethyl acetate. (2×200 ml). The combined organic extracts were washed with brine (200 ml), dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with pentane: ethyl acetate (95:5, by volume) to give (3-benzyloxy-phenyl)-acetic acid benzyl ester (10.7 g) as a white solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux under nitrogen for 44 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was partitioned between ethyl acetate (200 ml) and water (200 ml)
  7. extractionthe aqueous phase was extracted with ethyl acetate
  8. washThe combined organic extracts were washed with brine (200 ml)
  9. dry with materialdried over Na2SO4
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was purified by flash column chromatography on silica gel eluting with pentane: ethyl acetate (95:5, by volume)

Sources & evidence

ORD record
ord-310e282da54e44e8a9e253f479a34739
Source dataset
uspto-grants-2005_11
Patent number
US06967204B2

Reaction notes

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