Toluene → Cresyl saligenin

Participants

Reaction Steps

To a 500 ml round bottom flask containing 100 mL of THF under Ar was added commercial 1 M p-methylphenyl magnesium bromide/Et2O (100 mL, 100 mmol). Subsequently, salicylaldehyde (4.9 g, 40.3 mmol) was added dropwise in four equal portions spaced over 2 hr. After 20 min, once HPLC analysis revealed the aldehyde to be consumed, the reaction was quenched by dropwise addition of 26 ml of sat'd NH4Cl/H2O to produce a white paste. To this suspension was added 200 mL of PhMe and sufficient H2O to permit stirring. The organic layer was decanted whereupon the white paste was triterated a second time with 1:1 THF/PhMe. After decanting, the combined organic layers were concentrated using a rotary evaporator to obtain 9.7 g of crude 4-methyl-2′-hydroxybenzhydrol.

Provenance & Evidence