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

HRID 1576182ノート

反応式

HRID 1576182 の反応式
[CH2:1]1COC2(C3C=CC(CC#N)=CC=3C=CC3C=CC=CC2=3)O1.Cl.[CH:24]1[C:34]2[CH:33]=[CH:32][C:31]3[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=3[C:29](=[O:39])[C:28]=2[CH:27]=[CH:26][C:25]=1[CH2:40][C:41]([OH:43])=[O:42].C1COC2(C3C=CC(C(C)C#N)=CC=3C=CC3C=CC=CC2=3)O1>O.C(OCC)(=O)C.C(O)(=O)C>[CH:24]1[C:34]2[CH:33]=[CH:32][C:31]3[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=3[C:29](=[O:39])[C:28]=2[CH:27]=[CH:26][C:25]=1[CH:40]([CH3:1])[C:41]([OH:43])=[O:42]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 123988215-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acidHCID 123988235,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl acetonitrileHCID 214031012-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionitrile

生成物 1

HCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-収率 75%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

23.4 Gm. of 5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl acetonitrile is refluxed for seven hours in 160 ml. of acetic acid and 240 ml. of concentrated hydrochloric acid. The solution is cooled and added to ethyl acetate and water. The organic layer is washed with water then extracted with aqueous sodium carbonate. The extract is acidified with hydrochloric acid and extracted with ethyl acetate. The extract is dried and evaporated to afford the product which is recrystallized from acetone/hexane to give 9.5 gm., 50%, of 5H-dibenzo[a,d]cyclohepten-5-on-2-yl acetic acid, m.p. 148°-149.5°C. Use of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionitrile gives a 75% 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.

後処理

  1. temperatureThe solution is cooled
  2. washThe organic layer is washed with water
  3. extractionthen extracted with aqueous sodium carbonate
  4. extractionextracted with ethyl acetate
  5. customThe extract is dried
  6. customevaporated
  7. customto afford the product which
  8. customis recrystallized from acetone/hexane
  9. customto give 9.5 gm

出典と根拠

ORDレコード
ord-af8a10d81f6648958780b739d1e2fc14
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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