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The preparation and stereochemistry of 1‐chloroethyl‐4‐methyl‐6,7‐dimethoxyisochroman
Author(s) -
Mccall John M.,
Tenbrink Ruth E.,
Kamdar Bharat V.,
Chidester Constance
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160232
Subject(s) - chemistry , boron trifluoride , acetal , catalysis , ethanol , boron , organic chemistry , medicinal chemistry , stereochemistry
The boron trifluoride catalyzed reaction of 2‐methyl‐2‐(3,4‐dimethoxypbenyl)ethanol and chloropropionaldehyde diethyl acetal yields a mixture of cis and trans 1‐ehloroethyl‐4‐methyl‐6,7‐dimethoxyisochroman. The structure of the trans compound was established by X‐ray analysis. The trans compound equilibrates to a mixture of the cis and trans when exposed to boron trifluoride catalyst.