Hydroquinone → HCID 70473457, compound

Participants

Reaction Steps

To a solution of hydroquinone (2.0 g, 18.2 mmol) in MeOH (10 mL), KOH (1.02 g, 18.2 mmol) was added. Then 1,5-dibromopentane (3.1 mL, 22.7 mmol) was added dropwise over 10 min and the mixture was refluxed for 12 hours. The reaction mixture was concentrated, quenched with water (100 mL), and the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layer was washed water, brine, and dried over Na2SO4. The compound was purified by column chromatography to isolate intermediate 13a as a colorless oil (0.94 g, 3.26 mmol, 20% yield). 1H NMR (CDCl3, 400 MHz) δ 6.76-6.84 (m, 4H), 4.50 (s, 1H), 3.93 (t, J=6.4 Hz, 2H), 3.46 (t, J=6.4 Hz, 2H), 1.92-1.96 (m, 2H), 1.77-1.84 (m, 2H), 1.60-1.67 (m, 2H).

Provenance & Evidence