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

HRID 2399170Notes

Reaction equation

HRID 2399170 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 (5) wasdissolved in 2 liters methanol and hydrogenated at 3 atm. pressure over 60 g. Raney nickel catalyst. After hydrogen uptake was complete, the catalystwas 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, n25 = 1.4623.

Workup

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

Sources & evidence

ORD record
ord-4257e39eabe94733b9680670814ea1f9
Source dataset
uspto-grants-1977_05
Patent number
US04026894

Reaction notes

Loading…