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

HRID 23751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 23751
C[O:2][C:3]([C:5]1[S:6][C:7]([C:19]([O:21]C)=[O:20])=[C:8]2[C:13]=1[O:12][CH2:11][CH:10]([CH2:14][O:15]C(=O)C)[O:9]2)=[O:4].[OH-].[K+].O>C(O)C>[OH:15][CH2:14][CH:10]1[O:9][C:8]2=[C:7]([C:19]([OH:21])=[O:20])[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:13]2[O:12][CH2:11]1

Komponenten

5

Edukt 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 207580182-Acetoxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid dimethyl ester

Produkt 1

HCID 219583572-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. additionwas added upon continuous cooling
  2. customwere removed by distillation
  3. additionTo the remaining part of the reaction mixture, we dropwise added
  4. additiona mixture of ice (50 g) and concentrated hydrochloric acid (25 mL)
  5. stirringstirred
  6. filtrationThe mixture was then filtrated
  7. washthe residue was washed with water
  8. customSubsequent drying

Quellen und Nachweise

ORD-Eintrag
ord-dfad2cae5fe645fab0f916f102fe594e
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852830B2

Notizen zur Reaktion

Wird geladen…