Hydroquinone → HCID 70473457, compound

Temperature

70 °C

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 (3.09 mL, 22.7 mmol) was added dropwise over 10 min. After the addition was complete, the mixture was refluxed for 12 hours at 70° C. The reaction mixture was concentrated and quenched with water (100 mL), and then the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layer was washed with water, then brine, and dried over Na2SO4. The solvent was evaporated to give a colorless oil, which was purified by column chromatography to isolate intermediate 14a (0.94 g, 3.62 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).

1. additionAfter the addition
2. concentrationThe reaction mixture was concentrated
3. customquenched with water (100 mL)
4. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
5. washThe combined organic layer was washed with water
6. dry with materialbrine, and dried over Na2SO4
7. customThe solvent was evaporated
8. customto give a colorless oil, which
9. customwas purified by column chromatography

ORD record

ord-ef72359be7ea4f998f76e0a208958e7d

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394233B2