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

HRID 972984노트

반응식

HRID 972984 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

23.4 Gm. of 5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl acetonitrile is refluxed for 7 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.

후처리

  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

출처 및 근거

ORD 기록
ord-5fb0b6f640084994b32f2c3c7de341c5
출처 데이터셋
uspto-grants-1977_10
특허 번호
US04054579

반응 노트

불러오는 중…