Toluene → 1-(2,4-Dihydroxyphenyl)ethanone oxime

HRID 2112737Notes

Reaction equation

HRID 2112737 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH3:10].Cl.[NH2:13][OH:14].C1(C)C=CC=CC=1>N1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1/[C:9](=[N:13]\[OH:14])/[CH3:10]

Participants

5

Reactant 3

HCID 1140TolueneHCID 69902',4'-DihydroxyacetophenoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 1354004931-(2,4-Dihydroxyphenyl)ethanone oximeYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(2,4-Dihydroxyphenyl)ethanone (4.5 g, 29.6 mmol) was dissolved in pyridine (17 mL). Hydroxylamine hydrochloride (2.1 g, 29.6 mmol) was added in small portions over 10 minutes. The reaction mixture was stirred at room temperature over night, partitioned between ethyl acetate and H2O. The organic layer was washed with H2O and 0.2 M aqueous HCl respectively. The oily residue was treated with H2O, evaporated in vacuo to yield a white semi-solid residue which was treated with toluene and then evaporated in vacuo to give the sub-title compound (4.8 g) as a white solid.

Workup

  1. custompartitioned between ethyl acetate and H2O
  2. washThe organic layer was washed with H2O and 0.2 M aqueous HCl respectively
  3. additionThe oily residue was treated with H2O
  4. customevaporated in vacuo
  5. customto yield a white semi-solid residue which
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-773ebea1a8e1493394bc4ea50110f45b
Source dataset
uspto-grants-2009_04
Patent number
US07524856B2

Reaction notes

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