Methyl 4-hydroxy-3-(hydroxymethyl)benzoate is treated with a large excess of $CH X_{3} MgBr$ in dry ether (before $H X_{3} O X^{+}$ work-up). Count the moles of $CH X_{3} MgBr$ consumed per mole of the compound, taking each acidic O-H (phenolic or alcoholic) as consuming one mole and the ester as consuming two moles; ignore any other reaction. Give the integer.

Numerical answer type, tolerance 0.5.

Answer: 4

Count: phenolic OH = 1, benzylic alcohol OH = 1, ester = 2, so the total is 4 moles of

CH X_{3} MgBr

. The two O-H groups give methane and magnesium alkoxides/phenoxide; the ester adds two methyl groups to form a tertiary alkoxide.