تفاعل #1914817

معادلة التفاعل

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

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added upon continuous cooling
2. 2
   أخرىwere 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
   ترشيحThe mixture was then filtered
7. 7
   غسيلthe residue was washed with water
8. 8
   أخرىSubsequent drying

الإجراء التجريبي

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.

المصدر