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

HRID 1351967Notes

Reaction equation

HRID 1351967 reaction equation
[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.Cl>[OH-].[Na+]>[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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 239606Diethyl tetrahydropyran-4,4-dicarboxylate

Product 1

HCID 219303Dihydro-2H-pyran-4,4(3H)-dicarboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Diethyl tetrahydro-2H-pyran-4,4-dicarboxylate (4.04 g, 20 mmol) is suspended in a 30% aqueous sodium hydroxide solution (10 mL), and the mixture is stirred at room temperature for 28 hours. The pH value of the reaction solution is adjusted to pH 1 with conc. hydrochloric acid, and the mixture is separated into water and ethyl acetate. The organic layer is dried over anhydrous sodium sulfate, and the solvent is evaporated. Ethyl acetate (30 mL) is added to the obtained crude product, and the mixture is washed by repulping, and the resulting solid is collected by filtration, and dried to give tetrahydro-4H-pyran-4,4-dicarboxylic acid (3.19 g, 18.3 mmol, 92%).

Workup

  1. customthe mixture is separated into water and ethyl acetate
  2. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  3. customthe solvent is evaporated
  4. additionEthyl acetate (30 mL) is added to the
  5. customobtained crude product
  6. washthe mixture is washed
  7. filtrationthe resulting solid is collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-d471813f08b147ca962e4f7fd8269ef9
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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