Methanol → 2,3-Dihydro-4-(hydroxyimino)-2-phenyl-4H-1-benzopyran

HRID 1757951

Reaction equation

HRID 1757951 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=O)[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:27][OH:28]>O>[OH:28][N:27]=[C:11]1[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[O:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12]1

Participants

6

Reactant 4

HCID 887MethanolHCID 10251FlavanoneHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 2483142,3-Dihydro-4-(hydroxyimino)-2-phenyl-4H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,3-dihydro-2-phenyl-4H-1-benzopyran-4-one (50.0 g), methanol (535 ml), water (50 ml), potassium carbonate (59.3 g), and hydroxylamine HCl (59.8 g) was heated at reflux for 16 hours, then poured into ice-water; the oxime of 2,3-dihydro-2-phenyl-4H-1-benzopyran-4-one was filtered off, washed with water, then dried in air. Yield: 52 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. filtrationthe oxime of 2,3-dihydro-2-phenyl-4H-1-benzopyran-4-one was filtered off
  4. washwashed with water
  5. customdried in air

Sources & evidence

ORD record
ord-7e3eeb01189240eeb01b6d98e7b78069
Source dataset
uspto-grants-1983_02
Patent number
US04371541

Linked notes

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