Toluene → HCID 86689598, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-chloro-5-methoxynaphthalene (step-2 intermediate) (9.2 g, 47.8 mmol) in toluene (20 mL) and DMF (5.55 mL) at 0° C. was added, POCl3 (5.4 mL, 57.3 mmol) slowly. The reaction mixture was stirred at 0° C. for 45 min and then heated to reflux for 6-8 h. The dark red solution was cooled to RT and poured into a mixture of ice (50 mL) and 10% aq. NaOH (100 mL) with stirring. Aq. layer was extracted with EtOAc and the combined organic layer was washed with 2 N HCl, water, brine, dried and filtered. The solvent was evaporated and the crude product was washed with hexane, to provide the desired aldehyde intermediate as a reddish brown solid (2.1 g, 20%).

Provenance & Evidence