2-Bromoethanol → 2-[(6-Bromonaphthalen-2-yl)oxy]ethan-1-ol

Temperature

85 °C

To a solution of 6-bromo-2-naphthol (15.1 g, 67.7 mmol), 2-bromoethanol (10.11 g, 80.9 mmol) in N,N-dimethylformamide (60 ml) was added a solution of KOH (5.41 g, 81.9 mmol) and KI (0.37 g, 2.20 mmol) in water (10 ml). Upon stirring at 85° C. for 4 hours, the reaction mixture was filtered. The filtrate was shaken with diethyl ether (400 ml) and water (400 ml). The organic layer was washed with 2% KOH (100 ml water). The solvent was evaporated off to obtain crude product. Recrystallization from a mixed solvent of methanol (20 ml) and water (200 ml) yielded (h) in 10.0 g (55%). Proton-NMR spectral data (CDCl3), δ (ppm): 2.16 (t, HOCH2, 1H), 4.10 (m, HOCH2CH2, 2H), 4.22 (t, ArOCH2CH2,2H), 7.10-7.95 (m, aromatic, 6H).

1. filtrationthe reaction mixture was filtered
2. stirringThe filtrate was shaken with diethyl ether (400 ml) and water (400 ml)
3. washThe organic layer was washed with 2% KOH (100 ml water)
4. customThe solvent was evaporated off
5. customto obtain crude product
6. customRecrystallization from a mixed solvent of methanol (20 ml) and water (200 ml)

ORD record

ord-550bfb019cf64e0da4e5a42525e4d986

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06558572B2