Cesium carbonate → Methyl 2-[2-chloro-3-(hydroxymethyl)phenoxy]acetate

HRID 1250092Notes

Reaction equation

HRID 1250092 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[C:13]([CH2:14][OH:15])=[CH:12][CH:11]=[CH:10][C:9]=1[OH:16].Br[CH2:18][C:19]([O:21][CH3:22])=[O:20]>CC(C)=O>[CH3:22][O:21][C:19](=[O:20])[CH2:18][O:16][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([CH2:14][OH:15])[C:8]=1[Cl:7]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 155506102-Chloro-3-(hydroxymethyl)phenol

Product 1

HCID 15550611Methyl 2-[2-chloro-3-(hydroxymethyl)phenoxy]acetateYield 84.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Cesium carbonate (3.42 g, 10.5 mmol) was added to a solution of 2-chloro-3-hydroxymethylphenol (1.59 g, 10 mmol) in acetone at room temperature, and the reaction mixture allowed to stir for 30 minutes. Methyl bromoacetate (1.68 g, 11 mmol) was then added. The mixture was stirred overnight, filtered, and the filtrate was concentrated in vacuo. Purification of the residue by silica gel flash chromatography, eluting with dichloromethane/methanol, gave (2-chloro-3-hydroxymethylphenoxy)acetic acid methyl ester as a white crystalline solid (1.94 g, 84.1%).

Workup

  1. stirringThe mixture was stirred overnight
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification of the residue by silica gel flash chromatography
  5. washeluting with dichloromethane/methanol

Sources & evidence

ORD record
ord-d40e21d17c7846aab042d412fd4c3b10
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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