Acetone → 4-[(Allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane

HRID 1031399

Reaction equation

HRID 1031399 reaction equation
[CH3:1][C:2]([CH3:4])=O.[CH2:5]([O:8][CH2:9][CH:10]([OH:13])[CH2:11][OH:12])[CH:6]=[CH2:7].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH2:5]([O:8][CH2:9][CH:10]1[CH2:11][O:12][C:2]([CH3:4])([CH3:1])[O:13]1)[CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 78950Glyceryl Allyl Ether

Product 1

HCID 27801544-[(Allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane was prepared by mixing acetone, 225 parts, 3-allyloxy-1,2propanediol, 195 parts and toluene, 480 parts in a flask fitted with a magnetic stirring bar and a water trap mounted with a reflux condenser. Concentrated sulfuric acid, 4 parts, was added to the flask and the mixture was heated to reflux. The first 170 parts of distillate were removed via the water trap, after which reflux was conducted and water was collected in the water trap. After 13 hours the reaction mixture was cooled, neutralized with solid sodium bicarbonate, distilled to remove water and toluene and then distilled under vacuum to give 161 parts of 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane having a boiling point of 57° to 58° at 4.5 Torr.

Workup

  1. customThe 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane was prepared
  2. customfitted with a magnetic stirring bar and a water trap
  3. custommounted with a reflux condenser
  4. temperaturethe mixture was heated to reflux
  5. customThe first 170 parts of distillate were removed via the water trap
  6. temperatureafter which reflux
  7. customwater was collected in the water trap
  8. temperatureAfter 13 hours the reaction mixture was cooled
  9. distillationdistilled
  10. customto remove water and toluene
  11. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-7895716689e2440e872337b61331f79e
Source dataset
uspto-grants-1990_09
Patent number
US04954269

Linked notes

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