Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 22170578, compound

HRID 506159Notes

Reaction equation

HRID 506159 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.C1(C)C=CC(S(O[CH2:23][CH2:24][Cl:25])(=O)=O)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:23][CH2:24][Cl:25])[CH:6]=1

Participants

5

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 10796Cesium carbonateHCID 39129Methyl 3-Hydroxyphenylacetate

Product 1

HCID 22170578HCID 22170578, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 3-hydroxyphenylacetic acid methyl ester (22.6 g, 136 mmol) and 2-chloroethyl p-toluenesulfonate (40 g, 171 mmol) in 900 mL of acetone was added Cs2CO3 (88.8 g, 272 mmol) and the mixture was headed at reflux for 3 h. The reaction mixture was then cooled, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a gradient of 0-7% EtOAc in hexanes to yield 28.9 g (90% yield) of [3-(2-chloroethoxy)phenyl]-acetic acid methyl ester as a colorless oil.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with a gradient of 0-7% EtOAc in hexanes

Sources & evidence

ORD record
ord-8aacd05c6e3e45b89be42150a0cb9fe8
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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