Methyl Methacrylate → HCID 10773191, compound

HRID 582444Notes

Reaction equation

HRID 582444 reaction equation
[Na].[CH3:2][CH:3]([OH:7])[CH2:4][CH:5]=[CH2:6].[C:8](OC)(=[O:12])[C:9]([CH3:11])=[CH2:10]>CO>[C:8]([O:7][CH:3]([CH2:4][CH:5]=[CH2:6])[CH3:2])(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

5

Conditions

Temperature
100 °C

Procedure

Sodium metal (0.2 g) was dissolved in anhydrous methanol (3 g) and to this solution 4-penten-2-ol (18.5 g) was added followed by the addition of methyl methacrylate (50 g). The resulting mixture was stirred and heated until the methanol started to distill. The distilled methanol was collected at 64-70° C. After the removal of methanol was complete, the temperature was increased and at about 100° C. methyl methacrylate began to distill. At this moment, the reaction mixture was cooled to room temperature and was divided between dilute sulfuric acid (1N, 250 ml) and methylene dichloride (150 ml). The organic phase was then separated and washed with water and dried. Remaining solvents were removed and the residue was then fractionated under vacuum. Pure 4-penten-2-yl methacrylate was collected at 65-68° C./25 mmHg. Yield 17.5 g.

Workup

  1. additionwas added
  2. distillationto distill
  3. distillationThe distilled methanol was collected at 64-70° C
  4. customAfter the removal of methanol
  5. distillationto distill
  6. temperatureAt this moment, the reaction mixture was cooled to room temperature
  7. customThe organic phase was then separated
  8. washwashed with water
  9. customdried
  10. customRemaining solvents were removed
  11. customPure 4-penten-2-yl methacrylate was collected at 65-68° C./25 mmHg

Sources & evidence

ORD record
ord-33db1c6aeff245b2b9161a880cf220af
Source dataset
uspto-grants-1999_07
Patent number
US05925253

Reaction notes

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