Methanol → HCID 136401071, compound

HRID 987364Notes

Reaction equation

HRID 987364 reaction equation
C[CH:2]([CH2:6][CH:7]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)[CH2:8][CH2:9][CH2:10]C)[CH:3](O)C.S(O)(O)(=O)=O.[NH2:26][OH:27].[C:28]([O-])(=O)C.[Na+].[CH3:33][OH:34]>>[CH3:10][C:9]1[CH:8]=[C:7]([CH2:12][CH2:13][CH2:15][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:28])[CH:6]=[C:2]([CH:3]=[N:26][OH:27])[C:33]=1[OH:34]

Participants

5

Reactant 4

HCID 887MethanolHCID 159255Hydroxylamine, sulfate (1:1)HCID 517045Sodium AcetateHCID 70033491HCID 70033491, compound

Product 1

HCID 136401071HCID 136401071, compound

Procedure

3-Methyl-2-hydroxy-5-nonylacetophenone (2b) (102.5 g, 0.37 mol) was treated with hydroxylamine sulfate (36.44 g, 0.22 mol) and anhydrous sodium acetate (36.44 g, 0.44 mol) in methanol (150 mL) at reflux for 7 h. Crude product in the solvent was filtered and concentrated. The resulting oxime was converted to copper(II) complex and purified further by flash column chromatography. Pure fractions were pooled and treated with aqueous 200 gpl sulfuric acid. Removal of the solvent gave 3-methyl-5-nonylsalicylaldoxime.

Workup

  1. temperatureat reflux for 7 h
  2. filtrationCrude product in the solvent was filtered
  3. concentrationconcentrated
  4. custompurified further by flash column chromatography
  5. additiontreated with aqueous 200 gpl sulfuric acid
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-8e466a18971b488daa97c9c5bf6b8967
Source dataset
uspto-grants-2003_10
Patent number
US06632410B2

Reaction notes

Loading…