Über β‐[Oxy‐phenyl] ‐äthylamine und ihre Umwandlungen, VI. Mitteil.: Darstellung von β‐[Oxy‐phenyl] ‐äthylaminen mit freier phenolischer Hydroxylgruppe

Abstract

H a h n , 8 t i e hl: aber P-[Oxy-phenyll-athyline[ J h g . 71 Georg Hahn und Karl Stiehl: uber P-[Oxy-phenyll-athylamine und ihre Umwandlungen, VI. Mitteil.: Darstellung von @-[Oxy-phenyl] -athylaminen mit freier phenolischer Hydroxylgruppe *) .

The Preparation of Substituted Styrenes by Methods Not Involving Hydrocarbon Cracking.

“…In one p-acetoxy-/3-nitrostyrene preparation, besides the 11 per cent of the product obtained, there also was isolated 15 per cent of p-hydroxy-/3-nitrostyrene (68).…”

A Note on the Preparation of Some 1-Phenyl-2-Nitroethanol Derivatives

“…:~cetylatiori of S1,rinsnlrlrl1yclr AAttcmpts to prepare a number ol related nitroalcohols by this ~netliocl \\.ere not successlul: (i) vel-atralcleli) t l e g'lvc m a i d \ -:2,4-climetl1oxy-w-11itrostyrene, even after cooling the reaction mixture be10111 0"; (ii) protocatecliualdehyde, syringalclelij~cle, vanillin, and isovanillin did not react \\-it11 nitromethane under tlie above conditions. This is not altogether surprising in v i e \ \ of thc fact t h a t three of tliese aldehycles have a para liyclroxyl group, which has been 1 -c p o r t e t l by several worlcers to hinder this type of conclensation (1,8) ; (iii) : j , 4 -c l i b e n z o ) losybenzalclehycle, :3-benz~~loxy-4-1i1et110xybe11~:~1tlcl1j de, ~3,-l-clietl1osycarbo~loxybe1izaldeli~~de, ancl :i-etl1osycarbon~-loxy-4-11~ethoxybenzltleijcle gave oily proclucts, for 11-liich satisfactory :uialyses coulcl not be o b t a i l i e t l (lor the ~i i t r o a l c o l i o l ) even after (listillation i l l high v a c u u l i i . I t 117ould appear i n these cases that condensation l i :~t l occurred, b u t partial decomposition of the proclucts tool; place in tlie isolation or clistillation stages.…”