反応 #82996

反応方程式

octyl bromide

3,6-Dihydroxy xanthone

water

→

3-Octoxy-6-hydroxy xanthone

収率 30.0%

溶媒

methanol

methanol

反応条件

後処理

1. 1
   workup.DISSOLUTIONAfter the compound was completely dissolved
2. 2
   温度at refluxing temperature
3. 3
   その他giving a precipitate
4. 4
   ろ過This white precipitate was then filtered
5. 5
   洗浄washed with water
6. 6
   洗浄washed with hot hexane
7. 7
   その他to remove the disubstituted side product

実験手順

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).

出典