Réaction #1960522

Équation de réaction

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

Rendement 19.8%

Solvants

Methanol

water

water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with Ethyl acetate
2. 2
   Lavagewashed the organic layer with water
3. 3
   Séchagedried over Sodium sulphate
4. 4
   workup.DISTILLATIONdistilled under vacuum
5. 5
   Autreto get crude compound which
6. 6
   Autrewas purified by column chromatography

Mode opératoire

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).

Source