Acetic Acid → 2,6-Ditert-butyl-4-[(4-methoxyphenyl)methyl]phenol

Participants

Reaction Steps

2,6-Di-t-butyl-4-(4-methoxybenzyl) phenol was prepared as described for A above. A mixture of 2,6-di-t-butylphenol (51.5 g), 4-methoxybenzyl alcohol (34.5 g), formic acid (100 ml) and acetic acid (100 ml) was refluxed for 5 hours, diluted with water, and extracted with chloroform. Evaporation of the chloroform gave an oil which crystallized. Recrystallization from methanol gave colorless needles, mp 139° (58 g); (Found: C, 80.7; H, 9.30. Calc. for C22H30O2 : C, 80.9; H, 9.26%); pmr spectrum: δ1.42, 18H, S; δ3.79, 3H, S; δ3.86, 2H, S; δ5.04, 1H, S; δ6.83, 2H, D (J=8 Hz); δ6.98, 2H, S; δ7.12, 2H, D (J=8 Hz).

Provenance & Evidence