Recueil des Travaux Chimiques des Pays-Bas p. 325 - 330 (1988)
Update date:2022-07-30
Topics:
Cerfontain, Hans
Coenjaarts, Norbert J.
Koeberg-Telder, Ankie
The homogeneous sulfonation of 1,2-dihydroxybenzene (1), its monomethyl (2) and dimethyl ether (3) in concentrated aqueous sulfuric acid at 25 deg C has been studied and isomer distributions, as well as rate coefficients for the sulfonation of 1-3 and their monosulfonic acids, have been determined.In 73.5-87.5percent H2SO4, 1 yields the 3- and 4-sulfonic acids in a ratio of 25:75, 2 yields the 4-, 5- and 6-sulfonic acids in a ratio of 46:36:18 in 73.5percent H2SO4 and 50:39:11 in 87.5percent H2SO4, whereas 3 yields only the 4-sulfonic acid.The remarkable absence of the 3-sulfonic acid (< 2percent) with the 2-methoxy substrates 2 and 3 is discussed in terms of conformer populations of the reactants.In sulfuric acid <*>87.5percent H2SO4, the 4-sulfonic acid of 1 and the 5-sulfonic acid of 2 are present in part in the form of their hydrogen sulfate.In that acid region, the 3- and 4-sulfonic acids of 1 both yield the 3,5-disulfonic acid, the 4- and 6-sulfonic acids of 2 both yield the 4,6-disulfonic acid and the 4-sulfonic acid of 3 mainly yields the 4,6- together with some 4,5-disulfonic acid.
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Doi:10.1021/ml100017c
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(1959)Doi:10.1021/acs.orglett.7b00501
(2017)Doi:10.1021/acsmedchemlett.7b00107
(2017)Doi:10.1016/j.bmcl.2013.02.108
(2013)Doi:10.1016/S0040-4039(00)80482-7
(1988)