Réaction #52029

Équation de réaction

water

KOH

water

2-Acetoxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid dimethyl ester

→

2-hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added upon continuous cooling
2. 2
   Autrewere removed by distillation
3. 3
   workup.ADDITIONTo the remaining part of the reaction mixture, we dropwise added
4. 4
   workup.ADDITIONa mixture of ice (50 g) and concentrated hydrochloric acid (25 mL)
5. 5
   workup.STIRRINGstirred
6. 6
   FiltrationThe mixture was then filtrated
7. 7
   Lavagethe residue was washed with water
8. 8
   AutreSubsequent drying

Mode opératoire

2-Acetoxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid dimethyl ester (60 g, 0.18 mol) was dissolved in ethanol (680 mL). KOH (36 g) was added to this solution after which water (500 mL) was added upon continuous cooling. After addition of the water the reaction mixture was stirred for another 30 minutes after which the solvents were removed by distillation. To the remaining part of the reaction mixture, we dropwise added a mixture of ice (50 g) and concentrated hydrochloric acid (25 mL), and stirred. The mixture was then filtrated and the residue was washed with water. Subsequent drying resulted in quantitative formation of pure 2-hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid as demonstrated by NMR and mass spectroscopy.

Source