4-Hydroxybenzaldehyde → HCID 136018059, compound

HRID 1792749Notes

Reaction equation

HRID 1792749 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH2:10]([O:12][NH2:13])[CH3:11].ClCCl>O1CCOCC1>[CH2:10]([O:12][N:13]=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)[CH3:11]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 6344DichloromethaneHCID 69357Hydroxylamine, O-ethyl-

Product 1

HCID 136018059HCID 136018059, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-hydroxybenzaldehyde (100 mg, 0.88 mmol) and 50% O-ethylhydroxylamine aqueous solution (0.6 ml, 4.9 mmol) in dioxane (2 ml) was stirred under an atmosphere of argon at room temperature for 16 hours and then heated at 90-100° for 3 hours when thin layer chromatography (silica, dichloromethane) indicated the reaction was complete. The solution was evaporated to dryness and the residue partitioned between ethyl acetate (20 ml) and water (5 ml). The organic layer was washed with water, dried (Na2SO4) and evaporated to afford 4-hydroxybenzaldehyde O-ethyloxime (125 mg, 92.5%).

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue partitioned between ethyl acetate (20 ml) and water (5 ml)
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-631c2fe64f044b65aedaec9cf6bcb544
Source dataset
uspto-grants-2006_07
Patent number
US07078403B1

Reaction notes

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