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

HRID 972995Notes

Reaction equation

HRID 972995 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: δCDCl3 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-db7fa602e8f544eabbfb32ecc28a7e82
Source dataset
uspto-grants-1977_10
Patent number
US04054579

Reaction notes

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