Toluene → 5,7-Dimethylchroman-2-one

Participants

Reaction Steps

3-Acetyl-5-propyl-5,6,7,8-tetrahydro-2-naphthol (1) was reacted with adamantanone and pyrrolidine in toluene to give the corresponding derivative of the Example 2 compound (2) which was hydrolysed, with methanol containing a few drops of conc. hydrochloric acid, to the chromanone (3). Reduction of the chromanone (3) (2.7 g) with sodium borohydride (0.7 g) in methanol, gave the chromanol (4) (2.7 g), which was dehyrated by heating with anhydrous copper sulphate (1 g) to yield the product (5) colourless crystals from methanol (1.8 g).

Provenance & Evidence