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

HRID 257829Notes

Reaction equation

HRID 257829 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10])[CH2:5][OH: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 41816553-Chloro-4-hydroxy-5-methoxybenzyl alcoholHCID 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

To a solution of 0.500 g (2.65 mmol) of 3-chloro-4-hydroxy-5-methoxybenzyl alcohol (Bader) and 0.668 g (1.1 eq) of methyl 2-bromophenylacetate dissolved in 5 mL acetone was added 0.733 g (2 eq) of anhydrous potassium carbonate and the reaction mixture was stirred and refluxed overnight. The reaction mixture was cooled to room temperature, filtered and evaporated in vacuo. The residual oil was purified on a silica gel flash chromatography column eluted with 35% ethyl acetate/hexane to afford 0.570 g (64%) of the title compound.

Workup

  1. temperaturerefluxed overnight
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customThe residual oil was purified on a silica gel flash chromatography column
  5. washeluted with 35% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ada12f0014d54ed08e6ec5533f71c580
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Reaction notes

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