Benzaldehyde → 5,5-Bis(bromomethyl)-2-phenyl-1,3-dioxane

HRID 2073327Notes

Reaction equation

HRID 2073327 reaction equation
[Br:1][CH2:2][C:3]([CH2:8][Br:9])([CH2:6][OH:7])[CH2:4][OH:5].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S(=O)(=O)(O)O>C1C=CC=CC=1>[Br:1][CH2:2][C:3]1([CH2:8][Br:9])[CH2:6][O:7][CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:5][CH2:4]1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 1118Sulfuric AcidHCID 186922,2-Bis(bromomethyl)-1,3-propanediol

Product 1

HCID 218230705,5-Bis(bromomethyl)-2-phenyl-1,3-dioxaneYield 88.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2,2-Bis(bromomethyl)propane-1,3-diol (250 g) and benzaldehyde (110 g) were added to benzene (500 cm3) containing concentrated sulphuric acid (2 cm3) and the mixture boiled. Water was removed using a Dean Stark apparatus. After about 6 hours the reaction was complete. The mixture was cooled and the sulphuric acid neutralised by the addition of excess sodium bicarbonate. The resulting solution was filtered and the benzene removed under reduced pressure to give an oil which solidified on standing. Recrystallisation from petroleum ether gave the 1,3-dioxane (296 g) as a white solid (m.p. 66° C.).

Workup

  1. customWater was removed
  2. temperatureThe mixture was cooled
  3. additionthe sulphuric acid neutralised by the addition of excess sodium bicarbonate
  4. filtrationThe resulting solution was filtered
  5. customthe benzene removed under reduced pressure
  6. customto give an oil which
  7. customRecrystallisation from petroleum ether

Sources & evidence

ORD record
ord-4550d0a6d92b4106909d601e2b4b7037
Source dataset
uspto-grants-1990_04
Patent number
US04916214

Reaction notes

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