Selective deprotection of silyl-protected phenols using solid NaOH and a phase transfer catalyst

Article abstract of DOI:10.1016/S0040-4039(99)00459-1

Aryl silyl ethers can be deprotected to yield phenols in good to excellent yields using a biphasic system of 10 equivalents of NaOH and catalytic Bu₄NHSO₄ in 1,4-dioxane. Alkyl silyl ethers prepared using a variety of silyl protecting groups survive under these conditions, allowing selective deprotection of silyl-protected phenols in the presence of silyl- protected alcohols.