Hydroxylamine HCl → 4-Hydroxy-3-methylbenzonitrile

HRID 570803ノート

反応式

HRID 570803 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[CH3:10].[Cl-].O[NH3+:13]>C(O)(=O)C.C(OCC)C>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:13])=[CH:4][C:3]=1[CH3:10]

参加物

5

反応物 2

HCID 21645Hydroxylamine HClHCID 1399014-Hydroxy-3-methylbenzaldehyde

生成物 1

HCID 109645604-Hydroxy-3-methylbenzonitrile収率 66%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 4-hydroxy-3-methylbenzaldehyde (530 mg, 3.91 mmol) and hydroxyl ammonium chloride (406 mg, 5.81 mmol) in acetic acid (5 mL) was heated under reflux for 90 minutes. The cooled reaction mixture was then diluted with diethyl ether (30 mL) and washed with water (30 mL). The combined organic solution was washed with brine, dried over magnesium sulfate, concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol, 100:0 to 97.5:2.5, to afford the title compound as a pale yellow oil in 66% yield, 345 mg.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 90 minutes
  3. customThe cooled reaction mixture
  4. washwashed with water (30 mL)
  5. washThe combined organic solution was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by column chromatography on silica gel
  9. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-19a45a840d2d45c8817ec2f6ff16c09b
出典データセット
uspto-grants-2015_05
特許番号
US09023872B2

反応ノート

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