Toluene → 5-(2,3-Epoxypropyl)-5-hydroxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 2413017

반응식

HRID 2413017 반응식
[CH2:1]([C:4]1([OH:19])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3].C([O:24]O)(C)(C)C.C1(C)C=CC=CC=1>CCCCCC.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[V]>[O:24]1[CH2:3][CH:2]1[CH2:1][C:4]1([OH:19])[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2

참가 물질

6

반응물 3

HCID 1140TolueneHCID 6410tert-Butyl hydroperoxideHCID 905995-Allyl-10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ol

생성물 1

HCID 204314525-(2,3-Epoxypropyl)-5-hydroxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene수율 50%

시약·촉매·용매 2

HCID 5377225Vanadium(III) acetylacetonate촉매HCID 8058Hexane용매

실험 절차

To a stirred, refluxing solution of 35.7 g (0.14 mol) of 5-allyl-5-hydroxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene 10 (R. D. Hoffsommer, et al, supra) in 500 ml of hexane was added 0.5 g of vanadium (III) acetylacetonate followed by the dropwise addition of 25.1 g (0.22 mol) of 70% tert-butylhydroperoxide. The resulting yellow mixture was refluxed for 4 hrs., then 100 ml of toluene was added. The reaction was allowed to cool to room temperature and stand for 12 hrs. Excess hydroperoxide was destroyed by the addition of 300 ml of aqueous sodium sulfite (Na2SO3) solution (10%). The organic phase was separated, dried over anhydrous MgSO4, filtered and evaporated. Recrystallization of the solid from CHCl3 -hexane gave 18.5 g (50% yield) of the epoxide 11, m.p. 116°-118° C.

후처리

  1. temperatureThe resulting yellow mixture was refluxed for 4 hrs
  2. customExcess hydroperoxide was destroyed by the addition of 300 ml of aqueous sodium sulfite (Na2SO3) solution (10%)
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customRecrystallization of the solid from CHCl3 -hexane

출처 및 근거

ORD 기록
ord-92cf84b108054aae8b070cb79663080a
출처 데이터셋
uspto-grants-1985_01
특허 번호
US04495281

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