Methanol → 4-Ethyl-4-(Allyloxymethyl)-2,2 dimethyl-1,3 Dioxane

HRID 235678

Reaction equation

HRID 235678 reaction equation
C([O:4][CH2:5][CH:6]=[CH2:7])C=C.C[O:9][C:10]([O:13]C)([CH3:12])[CH3:11].[C:15]1([CH3:25])[C:16](S(O)(=O)=O)=[CH:17]C=[CH:19][CH:20]=1.CO>C1(C)C=CC=CC=1>[CH2:16]([C:15]1([CH2:25][O:4][CH2:5][CH:6]=[CH2:7])[CH2:20][CH2:19][O:13][C:10]([CH3:12])([CH3:11])[O:9]1)[CH3:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 64952,2-DimethoxypropaneHCID 69252-Methylbenzenesulfonic acidHCID 11194Diallyl ether

Product 1

HCID 220111684-Ethyl-4-(Allyloxymethyl)-2,2 dimethyl-1,3 DioxaneYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trimethololpropane monoallyl ether (174 g) was stirred in toluene (400 ml) with dimethoxypropane (110 g) and toluenesulfonic acid (1 g). The reaction mixture was heated until methanol distilled over and heating continued until distillate was no longer collected. Concentration and vacuum distillaiton (bp 85°-95° C., 1 mm Hg) gave the product in 94% yield.

Workup

  1. distillationdistilled over and
  2. temperatureheating
  3. customno longer collected
  4. concentrationConcentration and vacuum distillaiton (bp 85°-95° C., 1 mm Hg)
  5. customgave the product in 94% yield

Sources & evidence

ORD record
ord-1b94ba5e1bd94a539154634a2b41fc9f
Source dataset
uspto-grants-1987_02
Patent number
US04640940

Linked notes

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