Hydroxylamine HCl → 4-Hydroxy-3-methylbenzonitrile

HRID 570803Notes

Reaction equation

HRID 570803 reaction equation
[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]

Participants

5

Reactant 2

HCID 21645Hydroxylamine HClHCID 1399014-Hydroxy-3-methylbenzaldehyde

Product 1

HCID 109645604-Hydroxy-3-methylbenzonitrileYield 66%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-19a45a840d2d45c8817ec2f6ff16c09b
Source dataset
uspto-grants-2015_05
Patent number
US09023872B2

Reaction notes

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