Acetone → 5,5-Bis(bromomethyl)-2,2-dimethyl-1,3-dioxane

HRID 2196102Notes

Reaction equation

HRID 2196102 reaction equation
[Br:1][CH2:2][C:3]([CH2:8][Br:9])([CH2:6][OH:7])[CH2:4][OH:5].[CH3:10][C:11]([CH3:13])=O.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[Br:1][CH2:2][C:3]1([CH2:8][Br:9])[CH2:6][O:7][C:11]([CH3:13])([CH3:10])[O:5][CH2:4]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 186922,2-Bis(bromomethyl)-1,3-propanediol

Product 1

HCID 145372285,5-Bis(bromomethyl)-2,2-dimethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2,2-bis(bromomethyl)-1,3-propanediol (5.0 g, 19.1 mmol), anhydrous acetone (20 mL) and p-TsOH (100 mg) in benzene (75 mL) was refluxed for 12 h, with azeotropic removal of water. The reaction mixture was concentrated under reduced pressure, EtOAc (100 mL) was added and the organic layer was washed successively with H2O (3×30 mL) and brine (30 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The white solid obtained was triturated with n-pentane (20 mL) to afford 5,5-bis(bromomethyl)-2,2-dimethyl-[1,3]dioxane (521) as colourless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, EtOAc (100 mL)
  2. additionwas added
  3. washthe organic layer was washed successively with H2O (3×30 mL) and brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe white solid obtained
  8. customwas triturated with n-pentane (20 mL)

Sources & evidence

ORD record
ord-260ac4567d86429e9bcf0a4bd0879045
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

Loading…