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

HRID 972991Notes

Reaction equation

HRID 972991 reaction equation
C1CO[C:3]2([C:9]3[CH:10]=[CH:11][C:12]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:13][C:8]=3[CH:7]=[CH:6][C:5]3[CH:19]=[CH:20][CH:21]=[CH:22][C:4]2=3)[O:2]1.CC(C)=O>O>[CH:13]1[C:8]2[CH:7]=[CH:6][C:5]3[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=3[C:3](=[O:2])[C:9]=2[CH:10]=[CH:11][C:12]=1[CH:14]([CH3:18])[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 180AcetoneHCID 214030932-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid

Product 1

HCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-Yield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.0 Gm. of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid is dissolved in 20 ml. of acetone and to the solution is added 20 ml. of N-hydrochloric acid. The mixture is refluxed for 1 hour, then cooled, diluted with water, and extracted with ethyl acetate. The extract is washed, dried and evaporated to give a 90% yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid, m.p. (chloroform-hexane) 138°-139° C.; m.p. (acetone-hexane) 113°-115° C. Use of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)acetic acid gives a similar yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic acid, m.p. (acetone-hexane) 148°-149.5° C.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-dfb244a4c8cd45c2b43e2e39a8fce4f1
Source dataset
uspto-grants-1977_10
Patent number
US04054579

Reaction notes

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