Hydroquinone → 4-(3-Bromopropoxy)phenol

Temperature

70 °C

To a solution of hydroquinone (3.0 g, 27 mmol) in MeOH (30 mL), KOH (1.5 g, 27 mmol) was added. Then, 1,3-dibromopropane (3.3 mL, 32 mmol) was added dropwise over 10 minutes. 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 with washed water, thetn brine, and dried over Na2SO4. The solvent was evaporated and the product was purified by column chromatography to isolate the intermediate 10a (1.46 g, 6.31 mmol, 23% yield) as a pinkish solid. 1H NMR (CDCl3, 400 MHz) δ 6.81 (m, 4H), 5.93 (broad s, 1H), 4.06 (t, 2H), 3.61 (t, 2H), 2.30 (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. dry with materialthetn brine, and dried over Na2SO4
6. customThe solvent was evaporated
7. customthe product was purified by column chromatography

ORD record

ord-d4942f7c74c24fa781121b73d6d6cb7b

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394233B2