Sodium Hydroxide → 3-Chloro-alpha-methyl-4-(2-thienylcarbonyl)benzeneacetic acid

HRID 258891Notes

Reaction equation

HRID 258891 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15](C)([C:21](OCC)=O)[C:16]([O:18]CC)=[O:17])[CH:5]=[CH:6][C:7]=1[C:8](=[O:14])[C:9]1[S:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[C:8](=[O:14])[C:9]1[S:13][CH:12]=[CH:11][CH:10]=1)[CH:15]([CH3:21])[C:16]([OH:18])=[O:17]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 12232932HCID 12232932, compound

Product 1

HCID 1674493-Chloro-alpha-methyl-4-(2-thienylcarbonyl)benzeneacetic acid

Procedure

A mixture of 29.7 parts of diethyl 2-[3-chloro-4-(2-thenoyl)phenyl]-2-methylmalonate and 200 parts of sodium hydroxide solution 5% is stirred and refluxed for 5 hours. The reaction mixture is cooled and washed twice with 80 parts of benzene. The aqueous phase is acidified with concentrated hydrochloric acid solution and the product is extracted with chloroform. The extract is dried, filtered and evaporated. The oily residue is dissolved in 160 parts of ether. This solution is stirred with activated charcoal, filtered and evaporated. The oily residue is purified by column-chromatography, using a mixture of chloroform and 5% of methanol. The pure fractions are collected and the solvent is evaporated. The oily residue which solidifies on standing, is triturated in a mixture of benzene and petroleumether, yielding 3-chloro-4-(2-thenoyl)hydratropic acid; mp. 82.5° C; also named 3-chloro-4-(2-thenoyl)-α-methyl-phenylacetic acid.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureThe reaction mixture is cooled
  3. washwashed twice with 80 parts of benzene
  4. extractionthe product is extracted with chloroform
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe oily residue is dissolved in 160 parts of ether
  9. stirringThis solution is stirred with activated charcoal
  10. filtrationfiltered
  11. customevaporated
  12. customThe oily residue is purified by column-chromatography
  13. additiona mixture of chloroform and 5% of methanol
  14. customThe pure fractions are collected
  15. customthe solvent is evaporated
  16. customis triturated in a mixture of benzene and petroleumether

Sources & evidence

ORD record
ord-e0ee7a98f0b14ae9aa1ac38467594efb
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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