Ethanol → 3-[(2-Oxo-2-phenylethyl)thio]-5-(trifluoromethyl)benzoic acid

HRID 1606761Notes

Reaction equation

HRID 1606761 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[Na+].Cl[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].C(O)C>O>[CH2:18]([S:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)[C:5]([OH:7])=[O:6])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20]

Participants

6

Reactant 4

HCID 702EthanolHCID 107572-ChloroacetophenoneHCID 14798Sodium HydroxideHCID 21542284HCID 21542284, compound

Product 1

HCID 215444803-[(2-Oxo-2-phenylethyl)thio]-5-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.33 g. (6 m moles) of 3-mercapto-5-trifluoromethylbenzoic acid, 12 ml. of 1N sodium hydroxide solution and 930 mg. (6 m moles) of α-chloroacetophenone in 20 ml. of ethanol is allowed to stir at room temperature for 1 hour. The reaction mixture is diluted with water, extracted with ether and the resulting aqueous phase acidified with 12N hydrochloric acid. The light yellow oil which separates gradually crystallizes and is filtered, 1.8 g., m.p. 135°-150° C. A sample is sublimed at 165° C. and 0.05 mm pressure, m.p. 153°-155° C.

Workup

  1. additionA mixture of 1.33 g
  2. extractionextracted with ether
  3. customThe light yellow oil which separates gradually crystallizes
  4. filtrationis filtered
  5. customis sublimed at 165° C.

Sources & evidence

ORD record
ord-e36e3b0729484a2ea375cfaa31e9e3ec
Source dataset
uspto-grants-1976_04
Patent number
US03953595

Reaction notes

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