Acetone → 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester

HRID 1576193Notes

Reaction equation

HRID 1576193 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]([C:6]1[CH:24]=[CH:23][C:9]2[C:10]3(OCC[O:19]3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH:13]=[CH:14][C:8]=2[CH:7]=1)[CH3:5].CC(C)=O>O>[CH3:1][O:2][C:3](=[O:25])[CH:4]([C:6]1[CH:24]=[CH:23][C:9]2[C:10](=[O:19])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH:13]=[CH:14][C:8]=2[CH:7]=1)[CH3:5]

Participants

4

Reactant 2

HCID 180AcetoneHCID 537927402-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid methyl ester

Product 1

HCID 123988252-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 Gm. of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d] cyclohepten-2-yl)propionic acid methyl ester is dissolved in 10 ml. of acetone and to the solution is added 5 ml. of N-hydrochloric acid. The mixture is refluxed for one hour, then cooled, diluted with water, and extracted with ethyl acetate. The extract is washed with aqueous sodium carbonate and water, then dried and evaporated to afford a 75% yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester, as an oil which slowly crystallized, m.p. 37°-39°C., NMR: δCDCl 3 1.55(d), 3.67(s), 3.83(g), 7.04(s) ppm. Use of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d] cyclohepten-2-yl)acetic acid methyl ester gives a similar yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic acid methyl ester, m.p. 67°-69°C.

Workup

  1. temperatureThe mixture is refluxed for one hour
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with aqueous sodium carbonate and water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-9336a541753d4cf89bc51fa6ff1668ea
Source dataset
uspto-grants-1976_09
Patent number
US03979430

Reaction notes

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