Water → Dihydro-2H-pyran-4,4(3H)-dicarboxylic acid

HRID 1350106

Reaktionsgleichung

Reaktionsgleichung von HRID 1350106
[O:1]1[CH2:6][CH2:5][C:4]([C:12]([O:14]CC)=[O:13])([C:7]([O:9]CC)=[O:8])[CH2:3][CH2:2]1.[OH-].[K+].O>C(O)C>[O:1]1[CH2:2][CH2:3][C:4]([C:7]([OH:9])=[O:8])([C:12]([OH:14])=[O:13])[CH2:5][CH2:6]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 239606Diethyl tetrahydropyran-4,4-dicarboxylate

Produkt 1

HCID 219303Dihydro-2H-pyran-4,4(3H)-dicarboxylic acidAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a stirred solution of diethyl oxane-4,4-dicarboxylate (40.0 g., 173 mmol) in ethanol (100 mL) was added a solution of potassium hydroxide (21.4 g, 382 mmol) in ethanol (300 mL). After the completion of the addition, the reaction mixture was stirred for 15 min at ambient temperature and then refluxed for 2.5 h. Water (40 mL) was added to the thick, white suspension, and then the solvent was removed by rotary evaporation. Water (40 mL) was added to the remaining residue and the resulting mixture then acidified with concentrated sulfuric acid (20 mL). The acidic solution was extracted with diethyl ether (3×300 mL) and the combined organic layers were dried (Na2SO4). Removal of solvent by rotary evaporation yielded the product (27.3 g, 90.2% yield).

Aufarbeitung

  1. additionAfter the completion of the addition
  2. temperaturerefluxed for 2.5 h
  3. customthe solvent was removed by rotary evaporation
  4. additionWater (40 mL) was added to the remaining residue
  5. extractionThe acidic solution was extracted with diethyl ether (3×300 mL)
  6. dry with materialthe combined organic layers were dried (Na2SO4)
  7. customRemoval of solvent
  8. customby rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-e762fc4bd8dd4f2b89d573de74c01ee7
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214686B2

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