Methacrylic Acid → Tetrahydropyranyl methacrylate

HRID 483328Notes

Reaction equation

HRID 483328 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1>ClCCl>[C:1]([O:6][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 4093Methacrylic AcidHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 11041138Tetrahydropyranyl methacrylateYield 3.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

a solution of 25.0 g (290 mmol) methacrylic acid and 27.8 g (330 mmol) dihydropyran in 80 ml of dichloromethane was stirred for 14 hr at room temperature. The reaction mixture was thoroughly extracted with saturated aqueous sodium bicarbonate, dried (MgSO4) and concentrated in vacuo. The residue was distilled to give 1.84 g (10.8 mmol; 3.7% yield) tetrahydropyran-2-yl methacrylate, bp 53° C. at 0.2 torr.

Workup

  1. extractionThe reaction mixture was thoroughly extracted with saturated aqueous sodium bicarbonate
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. distillationThe residue was distilled

Sources & evidence

ORD record
ord-b5f51c19f03b4a718b0c6159e461d237
Source dataset
uspto-grants-1993_07
Patent number
US05225316

Reaction notes

Loading…