3,4-dihydro-2H-pyran-2-carboxylic acid → Oxane-2-carboxylic acid

HRID 47073Notes

Reaction equation

HRID 47073 reaction equation
[Na].[O:2]1[CH:7]=[CH:6][CH2:5][CH2:4][CH:3]1[C:8]([OH:10])=[O:9].[H][H]>CO.[Ni]>[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 1181403,4-dihydro-2H-pyran-2-carboxylic acidHCID 5360545SodiumHCID 178418361HCID 178418361, compound

Product 1

HCID 10964532Oxane-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

210 g. of the sodium salt of 3,4-dihydro-2H-pyran-2-carboxylic acid dissolved in 2 liters methanol and hydrogenated at 3 atmosphere pressure over 60 g. haney nickel catalyst. After hydrogen uptake was complete the catalyst was filtered and the solvents removed in vacuo. The residue was acidified with concentrated hydrochloric acid and extracted with chloroform. Distillation gave 143.8 g. product, b.p. 75°-80° C./0.4 mm ND25 =1.4633.

Workup

  1. filtrationwas filtered
  2. customthe solvents removed in vacuo
  3. extractionextracted with chloroform
  4. distillationDistillation
  5. customgave 143.8 g

Sources & evidence

ORD record
ord-66056dcd4e2a427281e6d5155758022c
Source dataset
uspto-grants-1979_11
Patent number
US04176191

Reaction notes

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