HCID 21403094, compound → 5-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

HRID 972992Notes

Reaction equation

HRID 972992 reaction equation
C(Cl)(Cl)Cl.CCCCCC.C1CO[C:13]2([C:19]3[CH:20]=[CH:21][C:22]([CH2:24][C:25]([OH:27])=[O:26])=[CH:23][C:18]=3[CH:17]=[CH:16][C:15]3[CH:28]=[CH:29][CH:30]=[CH:31][C:14]2=3)[O:12]1>CC(C)=O.CCCCCC>[CH:23]1[C:18]2[CH:17]=[CH:16][C:15]3[CH:28]=[CH:29][CH:30]=[CH:31][C:14]=3[C:13](=[O:12])[C:19]=2[CH:20]=[CH:21][C:22]=1[CH2:24][C:25]([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 21403094HCID 21403094, compoundHCID 21585165Chloroform hexane

Product 1

HCID 123988215-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

Reagents, catalysts & solvents 1

HCID 21880519Acetone hexaneSolvent

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.

Sources & evidence

ORD record
ord-f8a64576caf346248d761af7ab9eba00
Source dataset
uspto-grants-1977_10
Patent number
US04054579

Reaction notes

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