Sulfuric Acid → HCID 10881454, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 3-(prop-1-yloxy)benzoylacetate (745 g) (a compound of Formula (a)) in 1,2-dichloroethane was combined under nitrogen with a solution of 3-methoxyphenol (488 g) in 1,2-dichloroethane (2.5 L) and cooled to 0° C. Concentrated H2SO4 (626 mL) was added dropwise and the mixture was stirred vigorously at RT for 90 minutes. Ethyl acetate (3 L) and H2O (3 L) were added and the layers were equilibrated and separated. The aqueous layer was extracted again with ethyl acetate and the combined organic layers were washed with H2O, 5% aqueous Na2CO3, 5% aqueous NaOH, H2O, and brine (2 L each). The organic phase was dried with MgSO4 and concentrated to dryness to yield 841 g (86%) of 4-[3-(prop-1-yloxy)phenyl]-7-methoxycoumarin. The product was recrystallized from ethanol/isopropanol followed by ethyl acetate/isopropanol to give 533 g (63% recovery) of 4-[3′-(prop-1-yloxy)phenyl]-7-methoxycoumarin.

Provenance & Evidence