Water → 3-butoxy-6-hydroxy-9H-xanthen-9-one

Participants

Reaction Steps

3,6-Dihydroxy xanthone (1,60.7 mmol) was dissolved into hot basic water (Na2CO3 240 mmol in 600 ml water). After the 3,6-dihydroxy xanthone was completely dissolved, the temperature was controlled to 70° C. Isopropyl alcohol (10 ml) was added to the reaction mixture and butyl bromide (180 mmol) was added dropwise. The reaction mixture was stirred rigorously for 72 hours. A white precipitate appeared which was then filtered and washed with water. There was almost no disubstituted compound in the product. This precipitate was dissolved in 3% NaOH, filtered and finally reprecipitated with HCl yielding 90% of 3-butoxy-6-hydroxy xanthone.

Provenance & Evidence