Hydrochloric Acid → HCID 178490745, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-methoxyphenyl magnesium bromide was prepared by adding 27.7 g of m-bromoanisole to a suspension of magnesium turnings (3.6 g) in 150 ml of tetrahydrofuran (THF) dropwise over 1 hr. The mixture was heated at reflux for 2 hrs. The resulting solution was cooled to 5° C. and a solution of 4-chromanone (20.0 g) in 50 ml of dry THF added over 2 hrs. at 15° C. The resulting mixture was stirred overnight at room temperature, cooled to 10° C., and treated with 1N HCl until pH 7 was reached. The mixture was diluted with water, extracted twice with 500 ml of ether, and the combined extracts dried over MgSO4. Filtration and evaporation gave 29.6 g of the title compound as an oil. NMR (CDCl3); δ3.81 (S,3H), 4.80 (d,J=4 Hz, 2H) 5.76 (t,J=4 Hz, 1H), 6.7- 7.4 (M,8H).

Provenance & Evidence