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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence