2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)acetamide → 5-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

HRID 1576188Notes

Reaction equation

C(Cl)(Cl)Cl.CCCCCC.C1CO[C:13]2([C:19]3[CH:20]=[CH:21][C:22]([CH2:24][C:25](N)=[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:36].CCCCCC>>[CH:21]1[C:20]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:18]=[CH:23][C:22]=1[CH2:24][C:25]([OH:36])=[O:26]

Participants

Reactant 3

HCID 214030972-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)acetamide

HCID 21585165Chloroform hexane

HCID 21880519Acetone hexane

Product 1

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

Procedure

11.0 Gm. of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionamide is refluxed for 2 hours in 70 ml. of acetic acid and 105 ml. of concentrated hydrochloric acid. The mixture is cooled and diluted, then extracted with ether. The ethereal solution is extracted with aqueous sodium carbonate and the extract acidified and extracted with ethyl acetate 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)acetamide 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-1254e34af81944e5a8daecb86e4547e2
Source dataset: uspto-grants-1976_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03979430

Reaction notes

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