Water → 2-Cyanobenzocycloheptan-1-one

HRID 1595131

반응식

HRID 1595131 반응식
Br[CH:2]1[C:12](=[O:13])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3]1.[C-:14]#[N:15].[Na+].O.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>C1(C)C=CC=CC=1>[C:14]([CH:2]1[C:12](=[O:13])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3]1)#[N:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 8929Sodium CyanideHCID 26541Dibenzo-18-crown-6HCID 217033152-Bromobenzocycloheptan-1-one

생성물 1

HCID 217033162-Cyanobenzocycloheptan-1-one

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

2-cyanobenzocycloheptan-1-one (compound Ia) was prepared by dissolving 2-bromobenzocycloheptan-1-one (30.2 g, 0.126 mol) in toluene (150 mL) in a 500 mL round bottom flask equipped with a condenser. NaCN (18.6g, 0.38 mol), water (50 g), and dibenzo-18-crown-6 (0.5 g) were added to the flask. The reaction mixture was stirred vigorously at 90° C. under a static blanket of nitrogen for 15 hours. The reaction mixture was cooled and washed three times with water (70 mL×2+100 mL). The toluene solution was dried over sodium sulfate and filtered. The solvent was evaporated under reduced pressure. The residue was distilled under vacuum to give a yellow liquid (21.1 g, b.p. 158-162° C. at 17 mm Hg). The purity of the liquid was 96% by GC.

후처리

  1. customequipped with a condenser
  2. temperatureThe reaction mixture was cooled
  3. washwashed three times with water (70 mL×2+100 mL)
  4. dry with materialThe toluene solution was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. distillationThe residue was distilled under vacuum
  8. customto give a yellow liquid (21.1 g, b.p. 158-162° C. at 17 mm Hg)

출처 및 근거

ORD 기록
ord-6a2974bbb3c64a7fb1e377db2e187bfe
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06287749B1

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