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

HRID 978705

Reaction equation

HRID 978705 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.C1(C)C=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 mixture of 10 g of 2,2-bis(bromomethyl)-1,3-propanediol, 5 ml of acetone and a catalytic quantity (0.1 g) of p-toluenesulfonic acid was heated under reflux in 150 ml of benzene until the theoretical amount of water (0.8 ml) had been collected in a Dean-Stark trap (2 hours). Evaporation of the solvent gave 5,5-bis(bromomethyl)-2,2-dimethyl-1,3-dioxane (6A), as a solid, m.p.: 56°-58° C. The purity according to gas-liquid chromatography and proton NMR was 99%.

Workup

  1. customhad been collected in a Dean-Stark trap (2 hours)
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-994df256764a44c08adbb3675f3fd28f
Source dataset
uspto-grants-1987_05
Patent number
US04665197

Linked notes

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