Water → 2-Cyanobenzocycloheptan-1-one

HRID 1595131

反応式

HRID 1595131 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 217033162-Cyanobenzocycloheptan-1-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6a2974bbb3c64a7fb1e377db2e187bfe
出典データセット
uspto-grants-2001_09
特許番号
US06287749B1

関連ノート

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