That orthoboric acid is a tribasic acid is shown by the formation of ethyl orthoborate on esterification, the vapour density of which corresponds to the molecular formula B(0C2H5)3; the molecular formula of the acid must consequently be B(OH) 3 or H 3 B0 3.
Menschutkin (Ber., 1882, 15, p. 1 445; Ann., 1879, 1 95, p. 334) examined the rate of esterification of many acids with alcohols.
The investigation also showed that the nature of the acid used affected the result, for in an homologous series of acids it was found that as the molecule of the acid became more complex, the rate of esterification became less.
Meyer (Ber., 18 94, 2 7, p. 510 et seq.) showed that in benzenoid compounds ortho-substituents exert a great hindering effect on the esterification of alcohols by acids in the presence of hydrochloric acid, this hindering being particularly marked when two substituents are present in the ortho positions to the carboxyl group. In such a case the ester is best prepared by the action of an alkyl halide on the silver salt of the acid, and when once prepared, can only be hydrolysed with great difficulty.