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

HRID 490926ノート

反応式

HRID 490926 の反応式
[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]

参加物

5

反応物 3

HCID 74493-NitrobenzaldehydeHCID 9032Potassium Cyanide2 回HCID 23665763Sodium Bisulfite

生成物 1

HCID 32778082-Hydroxy-2-(3-nitrophenyl)acetonitrile収率 87.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-45957c185ce548db9d0459c71239a43e
出典データセット
uspto-grants-2009_05
特許番号
US07528173B2

反応ノート

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