Acetone → 5H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-

HRID 596537Notes

Reaction equation

HRID 596537 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:17]([CH3:20])[CH:18]=[O:19].CC(C)=[O:23].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>O>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:17]([CH3:20])[C:18]([OH:23])=[O:19]

Participants

5

Reactant 3

HCID 180AcetoneHCID 214093832-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanalHCID 131709961Jones' reagent

Product 1

HCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-Yield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.4 Gm. of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)-propionaldehyde is dissolved in 15 ml. of acetone and the solution is cooled to 0° C. under nitrogen. 0.4 ml. of 8N Jones reagent is added and the mixture is stirred for 2 hours, then diluted with water and extracted with ethyl acetate. The extract is washed with water then extracted with aqueous sodium carbonate. The aqueous solution is acidified with dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solution is dried and evaporated to yield 40% of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid, m.p. (chloroform-hexane) 138°-139° C.; m.p. (acetonehexane) 113°-115° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water
  3. extractionthen extracted with aqueous sodium carbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate solution is dried
  6. customevaporated

Sources & evidence

ORD record
ord-101000b4e7f04a789ea15131f7eebce6
Source dataset
uspto-grants-1977_03
Patent number
US04011243

Reaction notes

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