2-Hydroxy-4-methoxy-5-methylbenzaldehyde → 2-(1-Hydroxy-2-methyl-propyl)-5-methoxy-4-methyl-phenol

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Reaction Steps

The above prepared 2-hydroxy-4-methoxy-5-methyl-benzaldehyde (1.97 g, 11.86 mmol) was dissolved in 30 mL of abs. THF and treated at −15° C. with iPrMgCl (14.8 mL of 2M [THF], 2.5 eq.) and the mixture kept at this temperature for 0.5 h. Careful pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents left 2.45 g of the title compound as white crystals, almost perfectly pure according to TLC and NMR.

Provenance & Evidence