1,3-Propanediol → 2-(2-Bromophenyl)-1,3-dioxane

HRID 1881720Notes

Reaction equation

HRID 1881720 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:10](O)[CH2:11][CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[O:13][CH2:12][CH2:11][CH2:10][O:5]1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 811292-BromobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 108477842-(2-Bromophenyl)-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

ortho-Bromobenzaldehyde (4a) (8 g, 43.24 mmol) was stirred with 1,3 propanediol (4.7 ml, 64.86 mmol) and p-toluenesulfonic acid monohydrate (164 mg, 0.86 mmol) in benzene (150 ml) in a flask equipped with a Dean-Stark trap and a condenser. The mixture was heated at reflux for 12 hrs, cooled, and extracted with 2 M NaOH (100 ml), and brine (100 ml×3). The solution was dried over MgSO4, and the solvent evaporated to the title compound in quantitative yield.

Workup

  1. customequipped with a Dean-Stark trap and a condenser
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 12 hrs
  4. temperaturecooled
  5. extractionextracted with 2 M NaOH (100 ml), and brine (100 ml×3)
  6. dry with materialThe solution was dried over MgSO4
  7. customthe solvent evaporated to the title compound in quantitative yield

Sources & evidence

ORD record
ord-2392adcaa6e24e03a52a623dc451e650
Source dataset
uspto-grants-2012_11
Patent number
US08318938B2

Reaction notes

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