4-Hydroxybiphenyl → methyl (biphenyl-4-yloxy)acetate

HRID 1070391Notes

Reaction equation

HRID 1070391 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:15][C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:19][O:18][C:16](=[O:17])[CH2:15][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 10796Cesium carbonateHCID 60984Methyl bromoacetate

Product 1

HCID 2791909methyl (biphenyl-4-yloxy)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-phenyl phenol (5.00 g, 29.38 mmol) in acetone (100 mL) was added at room temperature, methyl bromoacetate (2.92 mL, 30.84 mmol) and cesium carbonate (14.36 g, 44.06 mmol). The mixture was stirred at room temperature for 5 h. The white precipitate was filtered and the filtrate was concentrated to dryness. Purification by flash chromatography (Hex:EtOAc/7:3) gave 6.76 g of (biphenyl-4-yloxy)-acetic acid methyl ester as a white solid.

Workup

  1. filtrationThe white precipitate was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customPurification by flash chromatography (Hex:EtOAc/7:3)

Sources & evidence

ORD record
ord-f021c79da94f413eb5daffeff73a157b
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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