Hydrochloric Acid → Tetrahydropyranyl methacrylate

HRID 483329Notes

Reaction equation

HRID 483329 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.Cl.C(=O)(O)[O-].[Na+]>[N+](C1C=C([N+]([O-])=O)C=CC=1C)([O-])=O.Cl>[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4093Methacrylic AcidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium Bicarbonate

Product 1

HCID 11041138Tetrahydropyranyl methacrylateYield 91%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 84612,4-DinitrotolueneCatalyst

Conditions

Temperature
50 °C

Procedure

to a solution of 25.8 g (0.3 mol) methacrylic acid and 1.8 g (0.011 mol) 2,4-dinitrotoluene in 25.2 g (0.3 mol) dihydropyran was added 0.05 ml (0.0015 mol) concentrated hydrochloric acid. The reaction mixture was allowed to stir at 50° C. for 25 hr. The hydrochloric acid was neutralized with solid sodium bicarbonate and the mixture was filtered. The filtrate was distilled to give 46.5 g (0.273 mol, 91% yield) tetrahydropyran-2-yl methacrylate, bp 50° C. at 0.15 torr.

Workup

  1. filtrationthe mixture was filtered
  2. distillationThe filtrate was distilled

Sources & evidence

ORD record
ord-a4b22e8e27be4e7fb3eadcb1543bfa82
Source dataset
uspto-grants-1993_07
Patent number
US05225316

Reaction notes

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