Benzyl Bromide → Methyl 2-(4-benzyloxyphenyl)acetate

HRID 460682Notes

Reaction equation

HRID 460682 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 2756645Methyl 2-(4-benzyloxyphenyl)acetateYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 15 g (90.3 mmol) of methyl 4-hydroxyphenylacetate in 25 mL of dimethylformamide (DMF) was added 32.4 g (99.3 mmol) of cesium carbonate, followed by 13.4 mL (112.9 mmol) of benzyl bromide (BnBr), and the resulting heterogeneous mixture was stirred at rt for 72 h. The reaction mixture was filtered, the solids were washed with ethyl acetate, and the combined organic extracts were concentrated to give a residue which was chromatographed on silica gel (25% hexane in dichloromethane) to afford 19.1 g (83% yield) of desired (4-benzyloxy-phenyl)-acetic acid methyl ester as indicated by 1H NMR; LC-MS—calcd for C16H16O3 [M++H]+: 257.11, found: 257.2.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solids were washed with ethyl acetate
  3. concentrationthe combined organic extracts were concentrated
  4. customto give a residue which
  5. customwas chromatographed on silica gel (25% hexane in dichloromethane)

Sources & evidence

ORD record
ord-c28de35a733d45f0b0923a0722dfaf4b
Source dataset
uspto-grants-2007_03
Patent number
US07196111B2

Reaction notes

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