Hydrochloric Acid → Oxane-4-carboxylic acid

HRID 902852Notes

Reaction equation

HRID 902852 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](C(OC)=O)([C:7]([O:9]C)=[O:8])[CH2:3][CH2:2]1.Cl>O>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11063483Dimethyl Tetrahydropyran-4,4-dicarboxylate

Product 1

HCID 219302Oxane-4-carboxylic acidYield 101.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethyl tetrahydro-4H-pyrane-4,4-dicarboxylate (4.04 g) was added to 20% hydrochloric acid (20 ml), and the mixture was heated under reflux for 19 hours. Water was added to the reaction mixture to conduct extraction with diethyl ether. After the resultant organic layer was washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. After the resultant residue was solidified with hexane, the resultant solides were collected by filtration and washed to obtain the title compound (2.63 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 19 hours
  3. extractionextraction with diethyl ether
  4. washAfter the resultant organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. filtrationthe resultant solides were collected by filtration
  8. washwashed

Sources & evidence

ORD record
ord-0a763e9b71d74c59ac0253cf0a7c1748
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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