Toluene → HCID 85381806, compound

Participants

Reaction Steps

44.44 Grams (0.02 moles) of α-(1-methylethyl)-3,4-dimethoxybenzeneacetaldehyde prepared in example 2 are dissolved in 180 ml of methanol, then 17.64 g (0.21 moles) of sodium bicarbonate are added and, finally, 14.60 g (0.21 moles) of hydroxylamine hydrochloride are added portionwise in 30 minutes. After stirring for an additional 30 minutes, 150 ml of toluene and 150 ml of water are added and the layers are separated. The aqueous phase is discarded. The toluene phases are collected together, washed with 50 ml of water, dried over anhydrous sodium sulphate, filtered and evaporated to dryness under vacuum. The oily residue is purified by treatment with heptane obtaining 43.40 g of oxime with a yield of 91.4%. An oxime sample crystallized three times from tetrachloroethylene, shows m.p.=89° C.÷91° C. and a 1H-NMR spectrum showing characteristic resonance peaks at the following δ (expressed as p.p.m.): 0.8 (d, 3H); 1.01 (d, 3H); 2.07 (m, 1H); 3.04 (t, 1H); 3.87 (2s, 6H); 6.76 (m, 3H); 7.54 (d, 1H).

Provenance & Evidence