Boron Trichloride → dimethyl 2-hydroxyisophthalate

Participants

Reaction Steps

A potassium salt of a phenol is needed for the next step in the reaction. The preferred potassium salt of a phenolic ester is made in two steps starting from commercially available 2-methoxyisophthalic acid. It is first reacted with trimethyloxonium tetrafluoroborate (Me3OBF4) and diisopropylethylamine ("iPr2NEt") under conditions effective to produce dimethyl 2-methoxyisophthalate. Gerecke, et al. Helv. Chim. Acta., 59:2551 (1976), which is hereby incorporated by reference. Then, the methyl ether is cleaved with BCl3 under conditions effective to yield dimethyl 2-hydroxyisophthalate. The potassium salt of dimethyl 2-hydroxyisophthalate is prepared by treating it with potassium hydride (KH) in toluene for about 20 minutes at about 0° C. under conditions effective to produce the potassium salt.

Provenance & Evidence