Phenothiazine → 2-Propenoic acid, 2-methyl-, 3-butenyl ester

HRID 582441Notes

Reaction equation

HRID 582441 reaction equation
[CH2:1]([OH:5])[CH2:2][CH:3]=[CH2:4].C1C2N[C:17]3[C:12](=CC=C[CH:16]=3)SC=2C=CC=1.[CH3:20][O-:21].[Mg+2].C[O-]>C(OC)(=O)C(C)=C>[C:20]([O:5][CH2:1][CH2:2][CH:3]=[CH2:4])(=[O:21])[C:17]([CH3:16])=[CH2:12]

Participants

5

Reactant 3

HCID 7108PhenothiazineHCID 693893-Buten-1-olHCID 164537Methanol, magnesium salt (2:1)

Product 1

HCID 5498832-Propenoic acid, 2-methyl-, 3-butenyl ester

Reagents, catalysts & solvents 1

HCID 6658Methyl MethacrylateSolvent

Procedure

To a 250 ml round-bottom flask, containing 3-buten-1-ol (24.7 g) and phenothiazine (0.1 g inhibitor), methyl methacrylate (80 ml) was added, followed by a methanolic solution of magnesium methoxide [prepared by dissolving magnesium metal (0.1 g) in anhydrous methanol (5 ml)]. The stirred mixture was slowly heated and methanol was distilled off (bp 64-70° C.) until the temperature at the distillation head rose to approximately 100° C. and the methyl methacrylate started to distill. The mixture was then cooled to room temperature and the solids were filtered off. The filtrate was fractionated under vacuum. Pure 3-butenyl methacrylate was collected at bp 63-66° C./30 mmHg. Yield: 22.5 g.

Workup

  1. additionwas added
  2. temperatureThe stirred mixture was slowly heated
  3. distillationmethanol was distilled off (bp 64-70° C.) until the temperature at the distillation head
  4. customrose to approximately 100° C.
  5. distillationto distill
  6. filtrationthe solids were filtered off
  7. customPure 3-butenyl methacrylate was collected at bp 63-66° C./30 mmHg

Sources & evidence

ORD record
ord-2c18349987de4bc097ec1be918b69d69
Source dataset
uspto-grants-1999_07
Patent number
US05925253

Reaction notes

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