Hydroquinone → HCID 12439901, compound

Temperature

70 °C

To a solution of hydroquinone (2.0 g, 18.2 mmol) in MeOH (20 mL), KOH (1.0 g, 18.2 mmol) was added. Then, 1,4-dibromobutane (2.7 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 the intermediate 12a (0.8 g, 3.26 mmol, 18% yield). 1H NMR (CDCl3, 400 MHz) δ 6.78 (s, 4H), 4.53 (s, 1H), 3.95 (t, J=6 Hz, 2H), 3.52 (t, J=6.8 Hz, 2H), 1.86-2.15 (m, 4H).

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-5d0bd136a0e54c919d6a9fa5f67284fb

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394233B2