Benzyl Bromide → Dimethyl 5-bentyloxy-isophthalate

Participants

Reaction Conditions

Reaction Steps

To a solution of dimethyl 5-hydroxyisophthalate (1 eq.) in DMF (0.5 M) at 0° C. was added portionwise NaH (1.2 eq.) and stirred for 30 min at 0° C. Benzyl bromide (1.2 eq.) was added and the reaction was stirred at rt for 1.5 h. The reaction was then quenched with water ( 1/7 volume), and the resulting precipitate was filtered and washed with hexane. The filtrate was diluted with ether and washed several times with water and brine. The organic extract was dried over MgSO4 and concentrated in vacuo to give a solid which was combined with the filtered precipitate to give dimethyl 5-(benzyloxy)isophthalate. This compound was subsequently dissolved in THF/MeOH (2:1, 0.5 M), and to this solution was added KOH powder. After stirring for 18 h at rt, the reaction was poured into a solution of ether/water. The two layers were separated and the ethereal layer was discarded. The aqueous layer was acidified to pH <1 with 3 N HCl and extracted with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated in vacuo to afford the title compound as a white solid.

Provenance & Evidence