Methanol → HCID 178487169, compound

Participants

Reaction Steps

A 500 mL one neck round bottomed flask equipped with a nitrogen inlet and provisions for magnetic stirring was charged with ethyl difluoroacetate (6.2 g, 50 mmol) and 75 mL of ether. To this solution was added 12 mL of 25% sodium methoxide in methanol (52.5 mmol). A solution of 6-methoxy-1-tetralone (8.81 g, 50 mmol) in 125 mL of ether was added over about 1 minute. The reaction mixture was stirred at room temperature for 14 hours and was diluted with 150 mL of 1N HCl. The phases were separated and the organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was taken up in 70 mL of boiling ethanol/water and cooled to room temperature, whereupon crystals of 2-[2,2-difluoro-1-hydroxyethylidene]-3,4-dihydro-6-methoxy-1(2H)-naphthalenone (also known as 6-methoxy-2-difluoroacetyl-1-tetralone) formed which were isolated by filtration and air dried (10.8 g, 85%): mp 52°-54° C.

Provenance & Evidence