3-Nitrobenzaldehyde → 2-Hydroxy-2-(3-nitrophenyl)acetonitrile

HRID 490926노트

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HRID 490926 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].S(=O)(O)[O-].[Na+].[C-:17]#[N:18].[K+]>CCOCC>[OH:8][CH:7]([C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:17]#[N:18]

참가 물질

5

반응물 3

HCID 74493-NitrobenzaldehydeHCID 9032Potassium Cyanide2회HCID 23665763Sodium Bisulfite

생성물 1

HCID 32778082-Hydroxy-2-(3-nitrophenyl)acetonitrile수율 87.4%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
10 °C

실험 절차

A mixture of m-nitrobenzaldehyde (27.0 g, 178.7 mmol) and a 10% solution of 24 g of sodium bisulfite was placed in a 2 liter flask and 75 mL of ether was added. The resulting mixture was cooled in an ice-bath to 10° C. and potassium cyanide (15.0 g, 230.3 mmol) in a 20% solution was added over a period of 30 minutes. The mixture was stirred for another 30 minutes after the addition of the potassium cyanide. The ether layer was separated and the aqueous layer was extracted with ether. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford 27.81 g (87%) of α-hydroxy-3-nitrobenzeneacetonitrile, a compound of formula (Q), as a pale yellow oil.

후처리

  1. customThe ether layer was separated
  2. extractionthe aqueous layer was extracted with ether
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-45957c185ce548db9d0459c71239a43e
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528173B2

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