3-Phenylphenol → Methyl(3-phenylphenoxy)acetate

HRID 2072581Notes

Reaction equation

HRID 2072581 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=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-].[K+].[K+]>CN(C=O)C.O>[C:1]1([C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[O:13][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 113813-PhenylphenolHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 13787157Methyl(3-phenylphenoxy)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-phenylphenol (5.00 g), methyl bromoacetate (3.1 ml) and potassium carbonate (8.1 g) in DMF was stirred at room temperature. After five hours, the reaction mixture was diluted with water (100 ml) and then extracted with ether. The combined organic layers were washed with aqueous sodium carbonate followed by brine and then dried, filtered and evaporated to give crude methyl (3-phenylphenoxy)acetate (7.2 g) as a pale yellow liquid, 1H NMR (CDCl3) delta 3.8 (3H,s), 4.7 (2H,s), 6.8-7.6 (9H,m) ppm.

Workup

  1. extractionextracted with ether
  2. washThe combined organic layers were washed with aqueous sodium carbonate
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-305bc901054e41edb770689a8a579347
Source dataset
uspto-grants-1990_04
Patent number
US04913721

Reaction notes

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