O-Xylene → HCID 13588806, compound

HRID 1905952Notes

Reaction equation

HRID 1905952 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH:7]([CH2:11][C:12]([OH:14])=O)[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.C1(C)C(C)=CC=CC=1>O>[CH3:1][C:2]1[S:6][C:5]2[CH:7]([C:8]([OH:10])=[O:9])[CH2:11][C:12](=[O:14])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 7237O-XyleneHCID 13588805HCID 13588805, compound

Product 1

HCID 13588806HCID 13588806, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

23.5 g of (5-methyl-2-thienyl) succinic acid was added to a mixture of 1.2 kg of polyphosphoric acid and 200 cc of xylene, previously heated to 100° C., and stirred for 3 hours at this temperature. After cooling to 80° C. the reaction mixture was poured in 4 liters of water and extracted with ethyl acetate. The organic phase was washed with water, dried on sodium sulfate then concentrated under reduced pressure. The residue was chromatographed on a silica column (successive eluants: 1/1 hexane-ethyl acetate, then 9/0.9/0.1 methylene chloride-ethanol-acetic acid). 5.7 g (yield: 26%) of 2-methyl-4oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid was obtained which was purified by recrystallization in a hexane-ethyl acetate mixture. Mp=140°-143° C.

Workup

  1. temperatureAfter cooling to 80° C. the reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. customdried on sodium sulfate
  5. concentrationthen concentrated under reduced pressure
  6. customThe residue was chromatographed on a silica column (successive eluants

Sources & evidence

ORD record
ord-ed9f8d5e584f4d7ca61c9b8f734bc785
Source dataset
uspto-grants-1987_03
Patent number
US04649153

Reaction notes

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