Hydrochloric Acid → HCID 12232943, compound

HRID 461706Notes

Reaction equation

HRID 461706 reaction equation
[CH3:1][C:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:26])[C:20]2[S:24][C:23]([CH3:25])=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(C(OCC)=O)[C:3]([O:5]CC)=[O:4].[OH-].[Na+].Cl>C1C=CC=CC=1>[CH3:25][C:23]1[S:24][C:20]([C:19]([C:16]2[CH:17]=[CH:18][C:13]([CH:2]([CH3:1])[C:3]([OH:5])=[O:4])=[CH:14][CH:15]=2)=[O:26])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12232929HCID 12232929, compound

Product 1

HCID 12232943HCID 12232943, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 15.5 parts of diethyl 2-methyl-2-[p-(5-methyl-2-thenoyl)phenyl]malonate and 120 parts of sodium hydroxide solution 5% is stirred and refluxed for 5 hours. The reaction mixture is cooled and shaken twice with 80 parts of benzene. The aqueous phase is acidified with concentrated hydrochloric acid solution. After standing for 10 minutes, the product is extracted with chloroform. The extract is washed with water, dried, filtered and evaporated. The residue is triturated in pertroleumether. The crude product is filtered off and purified by column-chromatography using a mixture of chloroform and 10% of methanol. The pure fractions are collected and the solvent is evaporated. The residue is crystallized from acetonitrile at -20 ° C, yielding p-(5-methyl-2-thenoyl)hydratropic acid; mp. 93.7° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionthe product is extracted with chloroform
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is triturated in pertroleumether
  9. filtrationThe crude product is filtered off
  10. custompurified by column-chromatography
  11. additiona mixture of chloroform and 10% of methanol
  12. customThe pure fractions are collected
  13. customthe solvent is evaporated
  14. customThe residue is crystallized from acetonitrile at -20 ° C

Sources & evidence

ORD record
ord-93fb3baf8b5d488e87a3009dd89557ef
Source dataset
uspto-grants-1977_12
Patent number
US04064132

Reaction notes

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