Methanol → HCID 12812398, compound

Participants

Reaction Conditions

Reaction Steps

60 mg of dibenzo-18-couronne-6 were added at 150° C. to a mixture of 10 ml of dioxane and 1.35 g of sodium hydride as a 50% oil suspension and then a solution of 0.61 ml of dichloroacetic acid in 10 ml of dioxane was added thereto over 5 minutes followed by addition of solution of 1.25 g of 2-hydroxy-5-chloro-α-methyl-benzhydrol in 5 ml of dioxane over 10 minutes at 20° C. The mixture was heated for 6 hours at 80° C., cooled to 20° C. and 2 ml of methanol were added thereto. The mixture was poured into iced water and was extracted three times with ethyl acetate. The organic extracts were washed 5 times with 0.1 N sodium hydroxide and the combined aqueous phases were acidified to a pH of 1 with 2 N hydrochloric acid and extracted 3 times with methylene chloride. The organic extracts were dried and evaporated to dryness to obtain raw 6-chloro-4-methyl-4-phenyl-[4H]-1,3-benzodioxin-2-carboxylic acid (mixture of two racemates diastereoisomers).

Provenance & Evidence