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

HRID 37820

Reaction equation

HRID 37820 reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7])C>C(O)C>[O:11]1[CH2:10][CH2:9][C:8]([C:6]([OH:7])=[O:5])([C:14]([OH:16])=[O:15])[CH2:13][CH2:12]1

Participants

4

Reactant 2

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

Product 1

HCID 219303Dihydro-2H-pyran-4,4(3H)-dicarboxylic acidYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6M potassium hydroxide solution (10 mL, 60 mmol) was added to an ice-cooled solution of tetrahydropyran-4,4-dicarboxylic acid diethyl ester (5 g, 21.7 mmol) in ethanol (40 mL) and heated at reflux overnight. The volatiles were evaporated, the residue diluted with water and acidified with conc. hydrochloric acid. The mixture was allowed to stand overnight then extracted with ether (3×25 mL). The combined ether layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford tetrahydro-pyran-4,4-dicarboxylic acid (2.3 g, 61%) as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe volatiles were evaporated
  4. additionthe residue diluted with water
  5. extractionthen extracted with ether (3×25 mL)
  6. washThe combined ether layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e930cfceb5d145fb9e9d191e999c6ac7
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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