Acetic Acid → 5H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-

HRID 1576187ノート

反応式

HRID 1576187 の反応式
C1CO[C:3]2([C:9]3[CH:10]=[CH:11][C:12]([CH:14]([CH3:18])[C:15](N)=[O:16])=[CH:13][C:8]=3[CH:7]=[CH:6][C:5]3[CH:19]=[CH:20][CH:21]=[CH:22][C:4]2=3)[O:2]1.Cl.C(O)(=[O:28])C>>[CH:13]1[C:8]2[CH:7]=[CH:6][C:5]3[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=3[C:3](=[O:2])[C:9]=2[CH:10]=[CH:11][C:12]=1[CH:14]([CH3:18])[C:15]([OH:16])=[O:28]

参加物

4

反応物 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 214030982-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionamide

生成物 1

HCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-収率 70%

実験手順

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.

後処理

  1. temperatureThe mixture is cooled
  2. additiondiluted
  3. extractionextracted with ether
  4. extractionThe ethereal solution is extracted with aqueous sodium carbonate
  5. extractionextracted with ethyl acetate

出典と根拠

ORDレコード
ord-fd87f389a8964a9ebde347dff5a38673
出典データセット
uspto-grants-1976_09
特許番号
US03979430

反応ノート

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