Benzophenone → 3,3-Diphenylacrylonitrile

반응식

[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[C:17](#[N:19])[CH3:18]>>[C:2]1([C:1]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:18][C:17]#[N:19])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

반응물 3

HCID 3102Benzophenone

HCID 6342Acetonitrile2회

HCID 14797Potassium Hydroxide

생성물 1

HCID 2743523,3-Diphenylacrylonitrile수율 73.3%

실험 절차

To a solution of benzophenone (9.1 g, 50 mmol) in acetonitrile (20 mL) was added potassium hydroxide (3.3 g, 50 mmol) in acetonitrile (25 mL). The solution was refluxed for 8 hours. The hot reaction mixture was poured into 100 g crushed ice and then extracted with dichloromethane. The organic extract was washed with water, dried over sodium sulfate, and concentrated in vacuo. The crude material was purified by flash column chromatography (diethyl ether/hexanes) to give 3,3-diphenylacrylonitrile (7.7 g, 73.3%) as an oil.

후처리

temperatureThe solution was refluxed for 8 hours
additionThe hot reaction mixture was poured into 100 g
customcrushed ice
extractionextracted with dichloromethane
extractionThe organic extract
washwas washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe crude material was purified by flash column chromatography (diethyl ether/hexanes)

출처 및 근거

ORD 기록: ord-f8097f9a50d0425c96c8f703a9bad69c
출처 데이터셋: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08629149B2

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