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

HRID 2237308Notes

Reaction equation

HRID 2237308 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>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1)[C:19]1[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)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxyphenylacetic acid (Acros, 3.04 g, 20 mmol) in 20 mL of DMF were added K2CO3 (6.90 g, 50 mmol) and benzyl bromide (4.75 mL, 40 mmol) at room temperature. The reaction mixture was stirred for 24 h. The suspension was filtered and washed with diethyl ether. The filtrate was then washed with brine and dried over MgSO4. Filtration, followed by concentration, provided the crude benzyl 2-(3-(benzyloxy)phenyl)acetate which was used in the next step. MS(ESI+) m/z 355 (M+Na)+.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with diethyl ether
  3. washThe filtrate was then washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration
  6. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-1f10b80cf9644ceaa8098d37c9ccb9df
Source dataset
uspto-grants-2010_05
Patent number
US07714138B2

Reaction notes

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