反応 #1960522

反応方程式

2-(6-nitrooxy-hexanoyloxy)-benzoic acid (2,2,5-trimethyl-[1,3]dioxan-5-yl carbamoyl)-methyl ester

p-toluenesulfonic acid

→

2-(6-Nitrooxy-hexanoyloxy)-benzoic acid (2-hydroxy-1-hydroxy methyl-1-methyl-ethylcarbamoyl)-methyl ester

収率 19.8%

溶媒

Methanol

water

water

反応条件

後処理

1. 1
   抽出extracted with Ethyl acetate
2. 2
   洗浄washed the organic layer with water
3. 3
   乾燥dried over Sodium sulphate
4. 4
   workup.DISTILLATIONdistilled under vacuum
5. 5
   その他to get crude compound which
6. 6
   その他was purified by column chromatography

実験手順

To a solution of 2-(6-nitrooxy-hexanoyloxy)-benzoic acid (2,2,5-trimethyl-[1,3]dioxan-5-yl carbamoyl)-methyl ester (5.5 grams) in a mixture of Methanol (55 ml) and water (2.5 ml), was added p-toluenesulfonic acid (0.2 grams) and stirred at room temperature for 2 hours. The reaction mixture poured onto cold water, extracted with Ethyl acetate, washed the organic layer with water, dried over Sodium sulphate and distilled under vacuum to get crude compound which was purified by column chromatography using Hexane:Ethyl acetate as eluant to get 1 grams of 2-(6-Nitrooxy-hexanoyloxy)-benzoic acid (2-hydroxy-1-hydroxy methyl-1-methyl-ethylcarbamoyl)-methyl ester as light yellow syrup. The product was characterized by 1H NMR (DMSO-d6) δ 1.16 (s, 3H, CH3), 1.45 (m, 2H, CH2), 1.70 (m, 4H, CH2X2), 2.64 (t, 2H, CH2), 3.50 (m, 4H, CH2X2), 4.55 (t, 2H, CH2), 4.70 (s, 2H, CH2), 4.80 (t, 2H, OH X2), 7.25 (d, 1H, Ar), 7.40 (m, 2H, Ar & NH), 7.70 (t, 1H, Ar), 8.00 (d, 1H, Ar).

出典