Hydroxyamine hydrochloride → HCID 11033419, compound

HRID 1070036Notes

Reaction equation

HRID 1070036 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>C(O)C>[OH:23]/[N:22]=[C:14](\[C:11]1[CH:12]=[CH:13][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1)/[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 2758881Ethyl 4-phenoxybenzoylformate

Product 1

HCID 11033419HCID 11033419, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-phenoxyphenylglyoxylate (37.9 g), hydroxylamine hydrochloride (11.7 g), sodium acetate (17.3 g) and ethanol (200 ml) was heated under reflux for 15 hours. The reaction mixture was concentrated, and the residue was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and then concentrated. The residual crystals were recrystallized from toluene-hexane to obtain ethyl E-2-hydroxyimino-2-(4-phenoxyphenyl)acetate (11.0 g, yield 28%) as a colorless oil. m.p. 131-132° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residual crystals were recrystallized from toluene-hexane

Sources & evidence

ORD record
ord-5cd954537744488481fce0b6a2d43566
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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