Potassium Carbonate → Methyl 2-(2-chloro-4-hydroxymethyl-6-methoxyphenoxy)-2-phenylacetate

HRID 1492578Notes

Reaction equation

HRID 1492578 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10])[CH:5]=[O:6].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([O:23][CH3:24])=[O:22].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]([O:11][CH3:12])[C:9]=1[O:10][CH:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:14]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 296223-Chloro-4-hydroxy-5-methoxybenzaldehydeHCID 8063364Methyl 2-(2-bromophenyl)acetate

Product 1

HCID 19385663Methyl 2-(2-chloro-4-hydroxymethyl-6-methoxyphenoxy)-2-phenylacetateYield 64%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.50 g (2.65 mmol) of 3-chloro-4-hydroxy-5-methoxy-benzaldehyde, 0.668 g (2.92 mmol) of methyl 2-bromophenylacetate and K2CO3 (0.73 g, 5.3 mmol) in acetone (8 mL) was refluxed for 14 h. The mixture was cooled, filtered and evaporated in vacuo, and the residue was purified by flash chromatography on a silica gel column using 5% ethylacetate in hexane to afford 0.570 g (64%) of the title compound.

Workup

  1. temperaturewas refluxed for 14 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customthe residue was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-0fca2eb8f8a8486aa5f63d019e701022
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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