Aluminum(III) Chloride → HCID 13588806, compound

HRID 1905954Notes

Reaction equation

HRID 1905954 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[S:10][C:9]([CH:11]2[CH2:16][C:15](=[O:17])[O:14][C:12]2=[O:13])=[CH:8][CH:7]=1>[N+](C1C=CC=CC=1)([O-])=O>[CH3:5][C:6]1[S:10][C:9]2[CH:11]([C:12]([OH:14])=[O:13])[CH2:16][C:15](=[O:17])[C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 13787398HCID 13787398, compound

Product 1

HCID 13588806HCID 13588806, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

21.1 g (0.16 mole) of aluminum chloride was quickly added to 50 cc of nitrobenzene at ambient temperature. Then a solution of 11.3 g (0.058 mole) of (5-methyl-2-thienyl) succinic anhydride in 30 cc of nitrobenzene was added drop by drop in 1 hour 30 minutes. The mixture was stirred for 5 hours at ambient temperature then poured into an ice-hydrochloric acid mixture and extracted with methylene chloride. The organic phase was separated and extracted with an aqueous solution of sodium carbonate. The aqueous phase was acidified with dilute hydrochloric acid then extracted with ethyl acetate. The organic solution was washed with water, dried on sodium sulfate and concentrated under reduced pressure. 7.7 g (yield=68%) of 2-methyl-4-oxo-5,6-dihydro-4H-cyclo-penta[b]thiophene-6-carboxylic acid melting at 137°-139° C. was obtained. By recrystallization in a hexane-ethyl acetate mixture, a product was obtained with a melting point of 140°-143° C. identical in all respects with that obtained in example 2.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic phase was separated
  3. extractionextracted with an aqueous solution of sodium carbonate
  4. extractionthen extracted with ethyl acetate
  5. washThe organic solution was washed with water
  6. customdried on sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c1a7478c43a45cbade70c063ee3120b
Source dataset
uspto-grants-1987_03
Patent number
US04649153

Reaction notes

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