Methacrylic Acid → Oxolan-2-yl 2-methylprop-2-enoate

HRID 1025258Notes

Reaction equation

HRID 1025258 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C12(CS(O)(=O)=O)[C:14](C)(C)[CH:11](CC1)[CH2:10][C:8]2=[O:9]>C(=O)(O)[O-].[Na+]>[C:1]([O:6][CH:14]1[CH2:11][CH2:10][CH2:8][O:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 4093Methacrylic AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

Product 1

HCID 154299Oxolan-2-yl 2-methylprop-2-enoateYield 4,001.8%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Methacrylic acid (86 g, 1 mol) was cooled to 15° C., and camphorsulfonic acid (4.6 g, 0.02 mol) was added thereto. 2-Dihydrofuran (71 g, 1 mol, 1.0 equivalents) was added dropwise to this solution. After stirring for 1 hour, saturated sodium bicarbonate (500 mL) was added, and the mixture was extracted with ethyl acetate (500 mL) and dried with magnesium sulfate; following this insoluble material was filtered, concentration under vacuum was then carried out at no greater than 40° C., and a yellow oily residue was distilled under vacuum, thus giving 125 g of tetrahydrofuran-2-yl methacrylate (MATHF) (yield 80%) as a colorless oily material, this being a fraction with a boiling point (bp.) of 54° C. to 56° C./3.5 mmHg.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (500 mL)
  2. dry with materialdried with magnesium sulfate
  3. filtrationwas filtered
  4. concentrationconcentration under vacuum
  5. customwas then carried out at no greater than 40° C.
  6. distillationa yellow oily residue was distilled under vacuum

Sources & evidence

ORD record
ord-8c26fa45ecdb42ebb8ca809fefa8f813
Source dataset
uspto-grants-2014_05
Patent number
US08728708B2

Reaction notes

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