Die Friedel‐Crafts'sche Ketonsynthese bei Phenoläthern

ANTIMALARIALS. α-PHENYL-β-DIALKYLAMINO ALCOHOLS1

“…The low yield (45%) may in part be explained by the formation of the by-product, 1, l-di-(p-butoxyphenyl)ethylene, (p-C.HgOCgH-t^C = CH2, a considerable amount of which was isolated from the reaction mixture. This type of compound has been reported by Gattermann and co-workers (43,44) in the preparation of p-methoxyacetophenone, and by Skraup and Nieten in the preparation of p-methoxybutyrophenone (45).…”

“…After stirring the suspension for two hours, the benzene layer was siphoned off, washed with water, dried, and treated with Norit. Evaporation of the benzene under reduced pressure gave 44 g. (25%) (m.p. 129-130°) which was sufficiently pure to use in the next step.…”

The Halogenation of Aryloxyacetic Acids and Their Homologs

“…Furthermore, the blocking of the free phenolic hydroxyl before the halogenation sometimes permits the introduction of halogen in positions other than those occupied in the free phenol. Similar observations have been recorded for certain substitution reactions in the 1-naphthol series (2,3,4). 1 Several instances of halogenation of phenyloxyacetic acid are known.…”

“…119-120°) prepared by Synerholm and Zimmermann (9) from the respective 4-chloro-2-methylphenol. 2 The halogenation seems, therefore, to deviate from the course it takes in the case of the free o-cresol.…”

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENEMETHANOLS. I. AMINO KETONE METHOD1

“…The synthesis of 4-haloacetonaphthones is described in the next paper (9). One trial of Noller and Adams' directions (21) for the synthesis of 2-methoxy-l-acetonaphthone by the Friedel and Crafts reaction between 2-methoxynaphthalene and acetic anhydride gave a low yield, and most of the material used was prepared from acetyl chloride (22) by a procedure involving remethylation of the crude reaction product with dimethyl sulfate before isolation. The yield was 50% and 21% of 2-methoxynaphthalene was recovered.…”