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

HRID 376560Notes

Reaction equation

HRID 376560 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8].[Na].[H][H]>O.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8]

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 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

3,4-Dihydro-2H-pyran-2-carboxylic acid, sodium salt (5.0g) in water (30ml) was treated with 10% Palladium on carbon catalyst (0.2g) and the mixture hydrogenated until there was no further uptake of hydrogen. The mixture was filtered through Kieselguhr, the filtrate passed through a column of 'Amberlite IR120(H+), evaporated in vacuo and the residue dissolved in dichloromethane, dried and evaporated to give the title compound as colourless oil. (3.3g, 76%); (Found: M+, 130.0631. C6H10O3 requires M, 130.0630; vmax (CH2Cl) 3500-2750 (v.br), 1772, 1725cm-1 ; δH (CDCl3), 1.5-1.7 (4H, m), 1.8-2.1 (2H, m), 3.50-3.59 (1H, m), 3.99-4.14 (2H, m) and 7.28 (1H, br.s).

Workup

  1. filtrationThe mixture was filtered through Kieselguhr
  2. customevaporated in vacuo
  3. dissolutionthe residue dissolved in dichloromethane
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-0f6e727a26ae42828361c4ea195043a0
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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