4-Chlorophenol → 1-Chloro-4-(2,2-diethoxyethoxy)benzene

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (11.24 g, 281 mmol) in anhydrous N,N-dimethylformamide (500 mL) was added 4-chlorophenol (30 g, 234 mmol) at 0° C. After hydrogen evolution had ceased, bromo-acetaldehyde diethyl acetal (55 g, 281 mmol) was added. The reaction was heated at 120° C. overnight. The mixture was poured into ice-water, extracted with ethyl acetate (3×150 ml), washed with 1N sodium hydroxide (3×100 ml), and brine (3×100 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum. The residue was purified by a silica gel column with 1% ethyl acetate in petroleum ether to afford 1-chloro-4-(2,2-diethoxyethoxy)benzene as oil (45 g, 75%).

Provenance & Evidence