2,6-DIMETHYLBENZOQUINONE 4-OXIME synthesis

Yield:4965-29-1 85%

Reaction Conditions:

with hydroxylamine hydrochloride;sodium acetate in ethanol; for 1.5 h;Reflux;

Steps:

5.3. General procedure for the oximation of the parabenzoquinones¹³

General procedure: NH2OH*HCl (0.221 g, 3.18 mmol) and NaOAc (0.169 g,2.08 mmol) were added to a solution of the para-benzoquinone (1.22 mmol) in EtOH (11.7 mL), and the resulting mixture was refluxed for 1.5 h. The solvent was evaporated under reduced pressure and the solid residue was diluted in water (50 mL), and extracted with a mixture of ethyl acetate and ethyl ether (1:1,320 mL). The organic phase was washed with a saturated solutionof NaHCO3 (320 mL) and brine (320 mL), dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The solid residue was washed with hexane (420 mL) to eliminate soluble impurities.

References:

Uliana, Marciana P.;Servilha, Bruno M.;Alexopoulos, Olga;De Oliveira, Kleber T.;Tormena, Cláudio F.;Ferreira, Marco A.B.;Brocksom, Timothy J. [Tetrahedron,2014,vol. 70,# 39,p. 6963 - 6973]