Dichloromethane → 4-Cyano-6,7-dimethyl-1-indanone

HRID 1608581

반응식

HRID 1608581 반응식
Br[C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([CH3:12])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:13].[Cu][C:15]#[N:16].C(Cl)Cl>CN(C=O)C.O.Cl.C1(C)C=CC=CC=1.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[C:15]([C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([CH3:12])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:13])#[N:16]

참가 물질

9

반응물 3

HCID 6344DichloromethaneHCID 138098694-Bromo-6,7-dimethyl-2,3-dihydro-1H-inden-1-oneHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 190422934-Cyano-6,7-dimethyl-1-indanone

시약·촉매·용매 5

HCID 16211236Trichloroiron;hexahydrate촉매HCID 313Hydrochloric Acid용매HCID 962Water용매2회HCID 1140Toluene용매2회HCID 6228Dimethylformamide용매

실험 절차

A mixture of 17.8 g (74.5 mmol) of 4-bromo-6,7-dimethyl-1-indanone [J. Het. Chem. 24, 677 (1987)] and 7.3 g (82 mmol) of copper(I) cyanide in 18 ml of DMF is stirred for 6 hours at 170°. The reaction mixture is then cooled to 100° and 200 ml of toluene and a solution of 31.2 g of iron(III) chloride hexahydrate in 47 ml of water and 8.2 ml of concentrated hydrochloric acid are added in succession thereto. The reaction mixture is stirred for 20 minutes at 70°, cooled and diluted with toluene and water. The organic phase is separated off, washed with water, a semi-saturated sodium hydrogen carbonate solution and again with water, dried and concentrated by evaporation. The residue is crystallised from ethyl acetate and ether and corresponds to starting compound (a). Beige crystals having a melting point of 160°-163° are obtained; IR (CH2Cl2): 2220, 1710 cm-1.

후처리

  1. temperatureThe reaction mixture is then cooled to 100°
  2. stirringThe reaction mixture is stirred for 20 minutes at 70°
  3. temperaturecooled
  4. customThe organic phase is separated off
  5. washwashed with water
  6. dry with materiala semi-saturated sodium hydrogen carbonate solution and again with water, dried
  7. concentrationconcentrated by evaporation
  8. customThe residue is crystallised from ethyl acetate and ether and corresponds
  9. customare obtained

출처 및 근거

ORD 기록
ord-055e89f5667443358541f709247e6755
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05395855

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