Water → Methyl Acrylate

HRID 1584038

Reaction equation

HRID 1584038 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[OH2:6]>[Al+3].[Cl-].[Cl-].[Cl-]>[CH3:2][O:1][C:5](=[O:6])[CH:4]=[CH2:3].[C:2]([CH:3]1[CH2:4][CH:2]2[O:1][CH:5]1[CH:4]=[CH:3]2)([O:1][CH3:5])=[O:6]

Participants

5

Reactant 2

HCID 962WaterHCID 8029Furan

Product 2

HCID 7294Methyl AcrylateYield 292.2%HCID 12271748Methyl 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Conditions

Temperature
20 °C

Procedure

1290 g (15 Mol) methylacrylate is prepared and 67.5 g (0.5 Mol) AlCl3 added thereto and dissolved with stirring. At 20° to 25° C., 1050 g (15.4 Mol) furane is added drop-wise during cooling. The temperature is maintained at 20° C. until the exothermic reaction is finished, after which stirring is continued for a further hour at 20° C. and then for 3 hours at 10° C. 300 g water is then added, the organic phase separated, and the unconverted furane and the methylacrylate distilled off under a pressure of 10 Torr and at a bath temperature of 60° C. in a rotary evaporator. Finally, the vacuum is lowered to 1 Torr and further volatile components drawn off. The crude product is passed to a thin-film evaporator under a vacuum of 1 Torr and a thermostatically controlled temperature of 95° C. A distillation temperature of approximately 70° C. is used. The 2-carbomethoxy-7-oxabicyclo(2,2,1)hept-5-ene is obtained in a yield of 1060 g (45.9% theoretical).

Workup

  1. dissolutiondissolved
  2. temperatureduring cooling
  3. stirringafter which stirring
  4. waitis continued for a further hour at 20° C.
  5. customthe organic phase separated
  6. distillationthe unconverted furane and the methylacrylate distilled off under a pressure of 10 Torr and at a bath temperature of 60° C.
  7. customin a rotary evaporator
  8. customThe crude product is passed to a thin-film evaporator under a vacuum of 1 Torr
  9. customa thermostatically controlled temperature of 95° C
  10. customA distillation temperature of approximately 70° C.

Sources & evidence

ORD record
ord-a289d304ea744587904277b0d0f30caa
Source dataset
uspto-grants-1985_11
Patent number
US04555581

Linked notes

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