Furan → Methyl 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate

HRID 1584037

Reaction equation

HRID 1584037 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH2:5]([O:7][C:8](=[O:11])[CH:9]=[CH2:10])C.[O:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1>>[C:8]([CH:9]1[CH2:10][CH:13]2[O:12][CH:16]1[CH:15]=[CH:14]2)([O:7][CH3:5])=[O:11]

Participants

4

Reactant 3

HCID 8029FuranHCID 8821Ethyl AcrylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12271748Methyl 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate

Procedure

4.5 g (0,033 Mol) AlCl3 are added to 100 g (1 Mol) ethylacrylate and dissolved with stirring. 68 g (1 Mol) furane is then added drop-wise, during cooling to 20° to 25° C. After one hour, the exothermic reaction is terminated, followed by stirring for one hour at 25° C. and 30 g water is added. The organic phase is separated. First, the non-converted furane and ethylacrylate is distilled off under a pressure of 10 Torr. The 2-carbomethoxy-7-oxabicyclo(2.2.1)hept-5-ene boils at 60° C. and is obtained in a yield of 67.2 g (40% theoretical).

Workup

  1. dissolutiondissolved
  2. temperatureduring cooling to 20° to 25° C
  3. customthe exothermic reaction
  4. customis terminated
  5. stirringby stirring for one hour at 25° C.
  6. addition30 g water is added
  7. customThe organic phase is separated
  8. distillationFirst, the non-converted furane and ethylacrylate is distilled off under a pressure of 10 Torr

Sources & evidence

ORD record
ord-846525d9bd8440ef838bce0f75d15d64
Source dataset
uspto-grants-1985_11
Patent number
US04555581

Linked notes

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