Ethanol → HCID 140402281, compound

Reaction equation

[CH3:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.C(O)C.Cl.[NH2:19][OH:20]>CCCCCC>[OH:20]/[N:19]=[C:4](\[C:3]1[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=1[CH3:1])/[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

Procedure

To a solution containing 19.2 g of ethyl 2-methylbenzoylformate (0.1 mol) and 100 ml of ethanol, 7.6 g of hydroxylamine hydrochloride (0.11 mol) was added and the resulting mixture was heated under reflux for 5 hours. Afterwards, the solvent was distilled off under reduced pressure as a work-up procedure to give a solid. The solid, to which hexane was added, was pulverized and 14.1 g of ethyl (E)-α-hydroxyimino-o-tolylacetate (yield; 68%) was filtered off. Furthermore, the concentrated residue of the filtrate, to which ethanol and a catalytic amount of thionyl chloride were added, was heated under reflux for 5 hours. The same work-up procedure as shown above was then employed to give 4.5 g of the objective product (yield; 21%). mp 88.0-89.0° C.