Potassium Carbonate → Methyl 2-(2-chloro-4-hydroxymethyl-6-propyl-phenoxy)-2-(3-chlorophenyl)acetate

HRID 1492642Notes

Reaction equation

HRID 1492642 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH2:11][CH2:12][CH3:13])[C:9]=1[OH:10])[CH2:5][OH:6].Br[CH:15]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)[C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([CH2:11][CH2:12][CH3:13])[C:9]=1[O:10][CH:15]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19385736Methyl 2-bromo-2-(3-chlorophenyl)acetateHCID 544827242-Chloro-4-(hydroxymethyl)-6-propylphenol

Product 1

HCID 54026416Methyl 2-(2-chloro-4-hydroxymethyl-6-propyl-phenoxy)-2-(3-chlorophenyl)acetateYield 80.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a magnetically stirred solution of 0.600 g (2.99 mmol) of the product of Step B in 6 mL acetone was added 0.869 g (3.30 mmol) of methyl α-bromo-(3-chlorophenyl)acetate, 0.829 g (6.00 mmol) of potassium carbonate and the reaction mixture was heated at reflux for 4 hours. The reaction mixture was cooled to room temperature, filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 15% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 0.925 g (80%) of the title compound.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified on a silica gel flash chromatography column
  6. washeluted with 15% EtOAc-hexane
  7. customEvaporation of the purified fractions
  8. customdrying in vacuo

Sources & evidence

ORD record
ord-e603f04487b2462cb886b05d4f25ac2d
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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