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A novel synthesis of 1‐(2,4,6‐trihydroxy‐3,5‐dimethylphenyl)ethanone (di‐ C ‐methylphloracetophenone) and two new non‐aromatic C ‐benzylated derivatives
Author(s) -
Hauteville Marcelle,
Stomberg Rolf,
Gaillard Pascale,
Duclos MarieChristine
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199509239
Subject(s) - chemistry , phloroglucinol , benzoyl chloride , benzyl chloride , chloride , acetyl chloride , organic chemistry , medicinal chemistry , catalysis
The synthesis of the title compound 1e was achieved by an easy three‐step procedure from 1,3,5‐benzenetriol ( 1a , phloroglucinol). Compound 1a was C ‐methylated using MeI. The crude mixture obtained was acetylated to give 1d which was converted into 1e using BF 3 AcOH complex. Benzylation of the latter with benzyl chloride afforded the new non‐aromatic compound 2 . Reaction of 2 with NaOH and benzoyl chloride (Scheme 1) gave the new compound 4 . Its structure was established by X‐ray analysis.