Acetic Acid → HCID 13588807, compound

HRID 1905956Notes

Reaction equation

HRID 1905956 reaction equation
C(O)(=O)C.[CH3:5][C:6]1[S:10][C:9]2[CH:11]([C:15]([OH:17])=[O:16])[CH2:12][C:13](=O)[C:8]=2[CH:7]=1.Cl>O.C1(C)C=CC=CC=1.[Zn]>[CH3:5][C:6]1[S:10][C:9]2[CH:11]([C:15]([OH:17])=[O:16])[CH2:12][CH2:13][C:8]=2[CH:7]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 13588806HCID 13588806, compound

Product 1

HCID 13588807HCID 13588807, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

6.5 cc of acetic acid was added to a suspension of 64.1 g (0.98 g at) of zinc powder and 6.4 g (0.024 mole) of mercuric chloride in 65 cc of water and the mixture was stirred for 30 min. Then a solution of 14 g (0.076 mole) of 2-methyl-4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid in 140 cc of toluene, then 60 cc of 10N hydrochloric acid were successively added. The mixture was refluxed for 5 hours then decanted after cooling to ambient temperature. The organic phase was separated. The aqueous phase was extracted with toluene. The organic solutions were collected, washed with water and dried on sodium sulfate. Evaporation of the solvent under reduced pressure provided 9.8 g (yield=71%) of 2-methyl-5,6-dihydro-4H-cyclo-penta[b]thiophene-6-carboxylic acid (mp=105°-107° C.) which was used afterwards without further purification. An analytical sample was obtained by recrystallization in a hexane-ethyl acetate mixture. Mp=107°-109° C.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. customthen decanted
  3. customThe organic phase was separated
  4. extractionThe aqueous phase was extracted with toluene
  5. customThe organic solutions were collected
  6. washwashed with water
  7. customdried on sodium sulfate
  8. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-58ae4b4e90b449bab8de67df77c53939
Source dataset
uspto-grants-1987_03
Patent number
US04649153

Reaction notes

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