Thionyl Chloride → HCID 18357785, compound

HRID 427989Notes

Reaction equation

HRID 427989 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12](O)[C:13]([O:15][CH3:16])=[O:14].S(Cl)([Cl:25])=O>ClCCCl>[Cl:25][CH:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][O:4][C:3]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:2]=1[CH3:1])[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18357788HCID 18357788, compound

Product 1

HCID 18357785HCID 18357785, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of methyl 2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-hydroxyacetate (0.50 g, 1.6 mmol) in 1,2-dichloroethane (20 ml) was stirred at room temperature. Thionyl chloride (0.61 g, 5.1 mmol) was added thereto, and the mixture was heated under reflux overnight and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=97/3) to give the desired compound methyl 2-chloro-2-[2-(2,5-dimethylphenoxymethyl)phenyl]acetate (0.35 g, 66%) as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=97/3)

Sources & evidence

ORD record
ord-c17f01915537455da3ef0d715dba7f16
Source dataset
uspto-grants-2001_11
Patent number
US06313150B1

Reaction notes

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