Water → 5-Acetyl-5-methyl-1,3-dioxane

HRID 892402Notes

Reaction equation

HRID 892402 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH3:7])[C:4](=[O:6])[CH3:5].[CH2:10]1OCOCO1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:4]([C:3]1([CH3:7])[CH2:8][O:9][CH2:10][O:1][CH2:2]1)(=[O:6])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 80811,3,5-TrioxaneHCID 5365163,3-Bis(hydroxymethyl)-2-butanone

Product 1

HCID 51479105-Acetyl-5-methyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3,3-bis(hydroxymethyl)-2-butanone (66.1parts) and s-trioxane (27 parts) in toluene (250 parts) containing p-toluenesulfonic acid (1.9 parts) is held under reflux while water of reaction is continuously removed (ca. 0.5 hr) by a Dean-Stark trap. The solution is cooled, neutralized by stirring with solid sodium bicarbonate and filtered Toluene is removed in vacuo and the residue distilled at 50-55° C. and 0.6 mm Hg. Proton NMR and combustion analysis are consistent with those values predicted for the desired product. Combustion Analysis for C7H12O3 --Calculated: C, 58.3%; H, 8.4%. Found: C, 57.9%; H, 8.2%.

Workup

  1. customis continuously removed (ca. 0.5 hr) by a Dean-Stark trap
  2. temperatureThe solution is cooled
  3. filtrationfiltered Toluene
  4. customis removed in vacuo
  5. distillationthe residue distilled at 50-55° C.

Sources & evidence

ORD record
ord-7f63e32c62124005acbb76283e70f768
Source dataset
uspto-grants-1992_06
Patent number
US05118599

Reaction notes

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