A one-pot synthesis of coumaryl, coniferyl and sinapyl alcohol

Article abstract of DOI:10.1016/S0040-4039(00)74358-9

The side chain of 4-allylphenol can be easily deprotonated if the butyl-lithium/potassium tert-butoxide superbase is employed. Consecutive treatment with fluorodimethoxyboron and hydrogen peroxide affords directly 3-(4-hydroxy-phenyl)-2-propen-1-ol ('coumaryl alcohol'). In the same way, 4-allyl-2-methoxyphenol can be converted to coniferyl alcohol and 4-allyl-2,6-dimethoxyphenol to sinapyl alcohol.