Acetic Acid → Diisopropylether methanol

Participants

Reaction Steps

A mixture of 5-methyl-2-oxindole (2.94 g, 0.02 mol), 3,5-di-tertiary-butyl-4-hydroxybenzoldehyde (4.68 g, 0.02 mol), and anyydrous NaOAc (5.75 g, 0.07 mol) in glacial acetic acid (100 mL) was heated to reflux for 18 hours. The cooled reaction mixture was poured into ice-water mixture when a yellow product precipitated out. It was recrystallized from CH2Cl2 --CH3OH-iso-Pr2O to give the analytical sample. Yield 2.16 g (28.7%), mp 230°-234° C.

Provenance & Evidence