1,4-Benzenedimethanol → 1,2-Benzenedimethanol

Participants

Reaction Steps

In a flask with dichloromethane (ca. 25 ml), 1,4-phenylenedimethanol (5 g, 0.036 mol) and levulinic acid (8.36 g, 0.072 mol) were mixed. The flask was then cooled in an ice water bath. Diisopropyl carbodiimide (9.09 g, 0.072 mol) and the catalyst DMAP (ca. 100 mg) were then added slowly to the solution. The mixture was allowed to come to room temperature and was stirred overnight. The mixture was then filtered and washed with 1M HCL brine. It was then dried over MgSO4 and concentrated in vacuo to afford a white solid as the product (9.5 g). Its purity was ascertained using 1H NMR (300 MHZ in CDCL3): δ 7.34 (s, 4H), 5.11 (s, 4H), 2.77 (t, 4H), 2.62 (t, 4H), 2.18 (s, 6H).

Provenance & Evidence