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

HRID 1763456Notes

Reaction equation

HRID 1763456 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) was dissolved in 2 liters methanol and hydrogenated at 3 atm. pressure over 60 g. Raney 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, n25 = 1.4623.

Workup

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

Sources & evidence

ORD record
ord-c6ac1875b94840dab03275a509663937
Source dataset
uspto-grants-1978_09
Patent number
US04112097

Reaction notes

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