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

HRID 1763888Notes

Reaction equation

HRID 1763888 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.Cl>O>[CH3:10][C:11]1([CH3:13])[O:7][CH2:6][C:3]([CH2:8][Br:9])([CH2:2][Br:1])[CH2:4][O:5]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric 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 962WaterSolvent

Procedure

The reactant 2,2-dimethyl-5,5-bis(bromomethyl)-1,3-dioxane was prepared by contacting 2,2-bis(bromomethyl) 1,3-propane diol with an excess of acetone in the presence of a catalytic amount of hydrochloric acid. Water produced in the reaction was removed with anhydrous calcium chloride and any residual acid was neutralized with sodium carbonate, the mixture filtered and the filtrate evaporated to dryness. The residue was extracted with carbon tetrachloride, filtered and the filtrate evaporated to give the desired 2,2-dimethyl-5,5-bis(bromomethyl)-1,3-dioxane reactant.

Workup

  1. customThe reactant 2,2-dimethyl-5,5-bis(bromomethyl)-1,3-dioxane was prepared
  2. customwas removed with anhydrous calcium chloride
  3. filtrationthe mixture filtered
  4. customthe filtrate evaporated to dryness
  5. extractionThe residue was extracted with carbon tetrachloride
  6. filtrationfiltered
  7. customthe filtrate evaporated

Sources & evidence

ORD record
ord-d629a3ac288c454daf4418d1c899516c
Source dataset
uspto-grants-1978_09
Patent number
US04113739

Reaction notes

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