Réaction #82996

Équation de réaction

octyl bromide

3,6-Dihydroxy xanthone

water

→

3-Octoxy-6-hydroxy xanthone

Rendement 30.0%

Solvants

methanol

methanol

Conditions de réaction

Traitement

1. 1
   workup.DISSOLUTIONAfter the compound was completely dissolved
2. 2
   Températureat refluxing temperature
3. 3
   Autregiving a precipitate
4. 4
   FiltrationThis white precipitate was then filtered
5. 5
   Lavagewashed with water
6. 6
   Lavagewashed with hot hexane
7. 7
   Autreto remove the disubstituted side product

Mode opératoire

3,6-Dihydroxy xanthone (1,20 mmol) was dissolved in hot mixture of basic water (80 mmol of Na2CO3 in 100 ml of water) and 50 ml of methanol. After the compound was completely dissolved, a methanol solution of octyl bromide (40 mmol in 50 ml of methanol) was added dropwise and the reaction mixture was stirred rigorously for 120 hours at refluxing temperature. The reaction mixture was cooled to room temperature giving a precipitate. This white precipitate was then filtered, washed with water, and washed with hot hexane to remove the disubstituted side product. 3-Octoxy-6-hydroxy xanthone was obtained in 30% yield. 1HNMR (DMSO): d11.0(1H,s), 8.05 (1H,d,J=6.0 Hz), 8.02 (1H,d,J=5.8 Hz), 7.08 (1H,s), 7.00 (1H,d,J=8.8 Hz), 6.89 (1H,d,J=8.8 Hz), 6.85 (1H,s), 4.43 (2H,t,J=6.2 Hz), 1.8(2H,M), 1.3 (10H,m), 0.9 (3H,t).

Source