Methanol → 1,3,5-Benzenetrimethanol

Participants

Reaction Steps

Trimethyl-1,3,5-benzenetricarboxylate 14 (1.98 g, 7.83 mmol) in dry THF (30 mL) was added through a pressure-equalized addition funnel into a stirring suspension of LiAlH4 (0.95 g, 24.9 mmol) in dry THF (65 mL) at 0° C. under an argon atmosphere. The mixture was allowed to warm to rt and stirred for 4 hours. 1H NMR (CDCl3) was used to monitor the reaction. After determining a large amount of starting material remained, additional LiAlH4 (0.50 g, 13.1 mmol) was added to the reaction mixture and the reaction was allowed to proceed at RT for an additional 4 hours. 1H NMR (CDCl3) was used to determine if reaction was complete. After the reaction was complete, MeOH (25 mL) was used to quench the reaction. The suspension was filtered using Celite and the Celite was washed with MeOH (100 mL). The filtrate was concentrated under reduced pressure. The residue was stirred in THF (30 mL), KHSO4 (3.53 g, 26 mmol) and Celite (1.53 g, 25.4 mmol) for 30 minutes. The suspension was filtered and washed with MeOH (50 mL). Solvents were removed under reduced pressure. The resulting solid was dissolved in hot ethyl acetate and filtered. The solid that remained at the filter was collected, dried and to yield triol 15 (0.954 g, 5.68 mmol, 73%). 1H NMR (DMSO): δ 7.22 (s, 3H), 5.17 (br s, 3H), 4.48 (s, 6H).

Provenance & Evidence