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Synthesis of aldehyde and carboxylic acid derivatives from 2‐hydroxymethyl‐3‐hydroxy‐4 H ‐pyran‐4‐one (α‐hydroxymaltol)
Author(s) -
Looker James H.,
Cliffton Michael D.
Publication year - 1986
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.5570230146
Subject(s) - chemistry , hydroxymethyl , aldehyde , pyran , acetic acid , carboxylic acid , ether , hydrogen bromide , bromide , organic chemistry , medicinal chemistry , acetone , catalysis , bromine
α‐Hydroxymaltol (2‐hydroxymethyl‐3‐hydroxy‐4 H ‐pyran‐4‐one) ( 1 ) has been converted to the 3‐ O ‐methyl ether 2 and 3‐ O‐p ‐nitrobenzyl ether 4 by standard methods. The ethers 2 and 4 have been oxidized by barium manganate to the corresponding aldehydes, 3 and 5 , in 91 and 77% yields respectively. Long‐term reaction of 5 with hydrogen bromide in acetic acid gives 3‐hydroxy‐4 H ‐pyran‐4‐one‐2‐carboxaldehyde ( 6 ). The aldehyde 3 is readily oxidized by short‐term reaction with silver oxide to the corresponding acid 7 .