Methyl 2-furoate → Methyl tetrahydrofuran-2-carboxylate

HRID 437114

Reaction equation

HRID 437114 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[H][H]>[Pd].CO>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 11902Methyl 2-furoateHCID 178418361HCID 178418361, compound

Product 1

HCID 169922Methyl tetrahydrofuran-2-carboxylateYield 89.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl furoate (50.4 g.) is dissolved in 180 ml. of methanol. Thereafter 1 g. of 5 percent palladium-on-charcoal is added. This mixture is then hydrogenated at 1 to 3 atmospheres. After 45 hours 0.79 moles of hydrogen are consumed. The black mixture is then filtered through Celite using 50 ml. of methanol to wash the reaction flask and filter. Evaporation of the filtrate under reduced pressure at 40°-45° C. bath temperature yields 51 g. of a yellow oil which is thereafter distilled, collecting that fraction boiling at 32°-35° C. Thereby, methyl tetrahydrofuroate (46.7 g.) is prepared.

Workup

  1. filtrationThe black mixture is then filtered through Celite
  2. washof methanol to wash the reaction flask
  3. filtrationfilter
  4. customEvaporation of the filtrate under reduced pressure at 40°-45° C. bath temperature
  5. customyields 51 g
  6. distillationof a yellow oil which is thereafter distilled
  7. customcollecting that fraction boiling at 32°-35° C

Sources & evidence

ORD record
ord-abaaecd28327439098188812c808990f
Source dataset
uspto-grants-1977_06
Patent number
US04029681

Linked notes

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