Furan → HCID 12914725, compound

HRID 1584039Notes

Reaction equation

HRID 1584039 reaction equation
Cl[Sn](Cl)(Cl)Cl.[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:9])[CH:7]=[CH2:8].[O:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1>O>[C:6]([CH:7]1[CH2:8][CH:16]2[O:15][CH:19]1[CH:18]=[CH:17]2)([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:9]

Participants

5

Reactant 3

HCID 8029FuranHCID 8846Butyl AcrylateHCID 24287Tin tetrachloride

Product 1

HCID 12914725HCID 12914725, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.3 g (0.013 Mol) SnCl4 is added to 64 g (0.5 Mol) butyl acrylate and dissolved with stirring. Then during cooling to 20° to 25° C., 34 g (0.5 Mol) furane is added drop-wise. The exothermic reaction finishes after one hour, after which stirring is continued for one hour at 25° C. and 30 g of water added. The organic phase is separated. First, the unconverted furane is distilled off under a pressure of 10 Torr, and then the residue is distilled under a pressure of 0.02 Torr. The 2-carbobutoxy-7-oxabicyclo(2.2.1)hept-5-ene boils at 65° C. and is obtained in a yield of 34.3 g (35% of the theoretical).

Workup

  1. dissolutiondissolved
  2. temperatureThen during cooling to 20° to 25° C.
  3. customThe exothermic reaction
  4. stirringafter which stirring
  5. waitis continued for one hour at 25° C.
  6. customThe organic phase is separated
  7. distillationFirst, the unconverted furane is distilled off under a pressure of 10 Torr
  8. distillationthe residue is distilled under a pressure of 0.02 Torr

Sources & evidence

ORD record
ord-10d0879b07fa44d6bc4b61d5f2bc39ad
Source dataset
uspto-grants-1985_11
Patent number
US04555581

Reaction notes

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