Thionyl Chloride → HCID 59627705, compound

HRID 1930116Notes

Reaction equation

HRID 1930116 reaction equation
[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]([CH3:15])=[C:6]([CH:8](O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=1.S(Cl)([Cl:20])=O>>[Cl:20][CH:8]([C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([O:16][CH3:17])=[CH:4][C:5]=1[CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 59627640HCID 59627640, compound2×

Product 1

HCID 59627705HCID 59627705, compoundYield 99.3%

Procedure

A solution of ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)-2-hydroxyacetate (Intermediate 3-6; 1.1 g, 4.25 mmol) in thionyl chloride (3.42 mL, 46.89 mmol) under nitrogen was stirred at 80° C. for 30 minutes. The reaction mixture was allowed to cool concentrated and diluted with water (20 mL), extracted with EtOAc (2×20 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford ethyl 2-chloro-2-(5-chloro-4-methoxy-2-methylphenyl)acetate (1.170 g, 99%) as a yellow gum.

Workup

  1. temperatureto cool
  2. concentrationconcentrated
  3. additiondiluted with water (20 mL)
  4. extractionextracted with EtOAc (2×20 mL)
  5. dry with materialthe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-98fe501c2ca6456d9e6b54e3d18b5a08
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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