Thionyl Chloride → HCID 86590586, compound

HRID 1884275Notes

Reaction equation

HRID 1884275 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:24](O)=[O:25])[C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.S(Cl)([Cl:30])=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:24]([Cl:30])=[O:25])[C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67483215HCID 67483215, compound

Product 1

HCID 86590586HCID 86590586, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-[2-carboxy-2-(4-cyclohexylphenyl)ethyl]-benzoic acid methyl ester (5.58 g, 15.2 mmol) in toluene was stirred and thionyl chloride (2.79 mL, 38.20 mmol) was added. The mixture was stirred and refluxed for 15 minutes and the toluene removed under reduced pressure. The residue was stripped twice with toluene to afford 5.75 g (98%) of 4-[2-chlorocarbonyl-2-(4-cyclohexylphenyl)ethyl]benzoic acid methyl ester.

Workup

  1. temperaturerefluxed for 15 minutes
  2. customthe toluene removed under reduced pressure

Sources & evidence

ORD record
ord-d1ca8e9c79a44c788edab5255c5a6d36
Source dataset
uspto-grants-2004_07
Patent number
US06762318B2

Reaction notes

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