Reacción #1914817

Ecuación de reacción

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

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added upon continuous cooling
2. 2
   Otrowere 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 HCl (25 mL)
5. 5
   workup.STIRRINGstirred
6. 6
   FiltraciónThe mixture was then filtered
7. 7
   Lavadothe residue was washed with water
8. 8
   OtroSubsequent drying

Procedimiento

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 HCl (25 mL), and stirred. The mixture was then filtered 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.

Fuente