Chloroform hexane → 5-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

HRID 972994Notes

Reaction equation

HRID 972994 reaction equation
C(Cl)(Cl)Cl.CCCCCC.C[O:12][C:13](=[O:34])[CH2:14][C:15]1[CH:33]=[CH:32][C:18]2[C:19]3(OCC[O:28]3)[C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=3[CH:22]=[CH:23][C:17]=2[CH:16]=1>CC(C)=O.CCCCCC>[CH:16]1[C:17]2[CH:23]=[CH:22][C:21]3[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=3[C:19](=[O:28])[C:18]=2[CH:32]=[CH:33][C:15]=1[CH2:14][C:13]([OH:34])=[O:12]

Participants

4

Reactant 2

HCID 21585165Chloroform hexaneHCID 54251221HCID 54251221, compound

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 methyl ester is stirred in 25 ml. of 1:1 concentrated sulfuric acid:water for 12 hours. The mixture is poured into water and extracted with ethyl acetate and the extract is washed, dried and evaporated to afford a 70% 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 methyl ester 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-c9c40eb3cf5341068d92e73e1ccaa029
Source dataset
uspto-grants-1977_10
Patent number
US04054579

Reaction notes

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