4-Hydroxybenzaldehyde → 4-Hydroxybenzaldehyde oxime

HRID 2228339Notes

Reaction equation

HRID 2228339 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][OH:11]>CO>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:10][OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 787Hydroxylamine

Product 1

HCID 2191304-Hydroxybenzaldehyde oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 500 ml round bottom flask equipped with a magnetic stirring bar, 40.49 g (331.6 mmol) of 4-hydroxybenzaldehyde were added. The aldehyde was dissolved in 240 ml methanol. To the stirred solution, 22.99 g (348.1 mmol) of 50% aqueous solution of hydroxylamine was added over a 15 min. period. The mixture was stirred for an additional 2 hr, at which time it was judged to be complete by the disappearance of the starting aldehyde as observed by thin layer chromatography (SiO2/CH3OH: CH2CL2 5:95). The solvent was removed in vacuo to give the product 4-hydroxybenzaldehyde oxime as a dark tan oil, which was recrystallized from water.

Workup

  1. customInto a 500 ml round bottom flask equipped with a magnetic stirring bar
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9851feca96f647a8a0bdcd5c74214d3b
Source dataset
uspto-grants-2002_07
Patent number
US06416696B1

Reaction notes

Loading…