HCID 12740016, compound → HCID 12740026, compound

HRID 648117Notes

Reaction equation

HRID 648117 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][C:9]=1[CH2:18][C:19]([OH:21])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>S1(CCCC1)(=O)=O>[O:21]=[C:19]1[C:7]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[CH2:1][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][C:9]=2[CH2:18]1

Participants

3

Reactant 1

HCID 12740016HCID 12740016, compound

Product 1

HCID 12740026HCID 12740026, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

To a mixture of 15 g of polyphosphoric acid and 10 ml of sulfolane was added 1.5 g of 2-benzyl-5-carboxymethylphenylacetic acid, and the mixture was heated at 100° to 110° C. for 2 hours with stirring. After the reaction, the reaction mixture was cooled, and dissolved in ice water. The solution was extracted with ethyl acetate, and washed with water. The ethyl acetate layer was extracted with a 2% aqueous solution of sodium hydroxide. The aqueous layer was acidified with 10% hydrochloric acid. The precipitated solid was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. The ethyl acetate was then distilled off. Recrystallization of the residue from a mixture of ethyl acetate and n-hexane afforded 0.52 g of 10,11-dihydro-10-oxo-5H-dibenzo[a,d]cycloheptene-2-acetic acid as a colorless crystalline powder having a melting point of 163° to 165° C.

Workup

  1. temperaturethe mixture was heated at 100° to 110° C. for 2 hours
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled
  4. extractionThe solution was extracted with ethyl acetate
  5. washwashed with water
  6. extractionThe ethyl acetate layer was extracted with a 2% aqueous solution of sodium hydroxide
  7. extractionThe precipitated solid was extracted with ethyl acetate
  8. washwashed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. distillationThe ethyl acetate was then distilled off
  11. customRecrystallization of the residue
  12. additionfrom a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-40da3152ce1c473e9f5099fffa9034aa
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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