Water → alpha-Methylthio-p-chlorophenylacetic acid

HRID 2286819Notes

Reaction equation

HRID 2286819 reaction equation
[Na].[CH3:2][SH:3].[OH-:4].[K+].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13](O)[C:14](Cl)(Cl)Cl)=[CH:9][CH:8]=1.[OH2:19]>C(O)C.C(OCC)C>[CH3:2][S:3][CH:13]([C:10]1[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=1)[C:14]([OH:19])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 214174-Chloro-alpha-(trichloromethyl)benzenemethanolHCID 45051789Methylmercaptan sodium

Product 1

HCID 23460389alpha-Methylthio-p-chlorophenylacetic acidYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A 20% aqueous solution of methyl mercaptan sodium salt (12.0 g, 34 mmoles) and potassium hydroxide (4.2 g, 66 mmoles) were dissolved in ethanol (25 ml). To the resulting mixture was added dropwise 1-(4-chlorophenyl)-2,2,2-trichloroethanol (4.0 g, 15.5 mmoles) dissolved in ethanol (10 ml) under water-cooling, and the mixture was stirred at room temperature for one day. Water and diethyl ether were added to remove any ether-soluble materials. The aqueous layer was rendered acidic with dilute hydrochloric acid, extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated and purified by silica gel column chromatography to afford 2.1 g of α-methylthio-p-chlorophenylacetic acid. Yield 62%.

Workup

  1. temperaturecooling
  2. customto remove any ether-soluble materials
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-c9ed9f7ee3814d4fa3520f0dee3b83e7
Source dataset
uspto-grants-1981_05
Patent number
US04268442

Reaction notes

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