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

HRID 483330Notes

Reaction equation

HRID 483330 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[O:7]1[CH:11]=[CH:10][CH2:9][CH2:8]1>ClCCl>[C:1]([O:6][CH:8]1[CH2:9][CH2:10][CH2:11][O:7]1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 4093Methacrylic AcidHCID 709342,3-Dihydrofuran

Product 1

HCID 154299Oxolan-2-yl 2-methylprop-2-enoateYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 10 g methacrylic acid in 10 ml dichloromethane was added a solution of 9.28 ml 2,3-dihydrofuran in 30 ml dichloromethane. The reaction was allowed to stir for 14 hr at room temperature. The mixture was washed with a saturated solution of sodium bicarbonate. The organic layer was dried with MgO/MgSO4 and concentrated in vacuo. The residue was distilled at 38° C./0.3 torr, to give 6.2 g (34% yield) of tetrahydrofuran-2-yl methacrylate. A solution of 6.0 g tetrahydrofuran-2-yl methacrylate and 0.066 g AIBN in 6 ml of MEK was heated to 60° C. for two days and 12 ml of MEK was added. This solution was used for further evaluation.

Workup

  1. washThe mixture was washed with a saturated solution of sodium bicarbonate
  2. dry with materialThe organic layer was dried with MgO/MgSO4
  3. concentrationconcentrated in vacuo
  4. distillationThe residue was distilled at 38° C./0.3 torr

Sources & evidence

ORD record
ord-ba73ed4df4354b9abdbe165b5e32dab0
Source dataset
uspto-grants-1993_07
Patent number
US05225316

Reaction notes

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