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

HRID 270084Notes

Reaction equation

HRID 270084 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 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(2,4-dihydroxyphenyl)ethanone (4.5 g, 29.6 mmol) was dissolved in pyridin (17 mL). Hydroxylamine hydrochloride (2.1 g, 29.6 mmol) was added in small portions over 10 minutes. After stirring at room temperature over night the green-yellowish solution was partitioned between water and ethyl acetate. The organic phase was washed twice with water and once with 0.2 M hydrochloric acid, and was finally concentrated. The oily residue was treated with water, evaporated to yield a white semi solid residue, which was treated with toluene and evaporated to give the titled compound (4.8 g, 98%) as a white solid.

Workup

  1. customwas partitioned between water and ethyl acetate
  2. washThe organic phase was washed twice with water and once with 0.2 M hydrochloric acid
  3. concentrationwas finally concentrated
  4. additionThe oily residue was treated with water
  5. customevaporated
  6. customto yield a white semi solid residue, which
  7. customevaporated

Sources & evidence

ORD record
ord-fe3f1c66162e4049bbed632f431c192d
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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