Hydroquinone → HCID 70473457, compound

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).

1. temperaturethe mixture was refluxed for 12 hours
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 water, brine
6. dry with materialdried over Na2SO4
7. customThe compound was purified by column chromatography

ORD record

ord-afff386937d0442b90be6dc8ab84cbc2

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394233B2