Methacrylic Acid → Tetrahydropyranyl methacrylate

HRID 1029350Notes

Reaction equation

HRID 1029350 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-4f0348ab97474bf7a6e5dac047aeb321
Source dataset
uspto-grants-1992_04
Patent number
US05102771

Reaction notes

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