Methacrylic Acid → Tetrahydropyranyl methacrylate

HRID 1034128Notes

Reaction equation

HRID 1034128 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-e4de4e9bff8343d4804f293f345d5b8d
Source dataset
uspto-grants-1994_05
Patent number
US05314785

Reaction notes

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