Water → 2-(3-Bromophenyl)-1,3-dioxane

HRID 85177Notes

Reaction equation

HRID 85177 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10](O)[CH2:11][CH2:12][OH:13].O>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:13][CH2:12][CH2:11][CH2:10][O:6]2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 104421,3-PropanediolHCID 765833-Bromobenzaldehyde

Product 1

HCID 101058152-(3-Bromophenyl)-1,3-dioxaneYield 102.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture containing 3-bromobenzaldehyde (135; 18.5 g, 100 mmol), propane-1,3-diol (9.1 g, 120 mmol) and TsOH (0.1 g) in toluene (200 mL) was stirred under reflux in a Dean-Stark water separator for 18 h. Upon cooling to room temperature, the mixture was washed with 5% aqueous Na2CO3 (200 mL), dried (Na2SO4) and concentrated under reduced pressure to afford essentially quantitative yield of crude 2-(3-bromophenyl)-1,3-dioxane 136 as a yellow oil (25 g).

Workup

  1. washthe mixture was washed with 5% aqueous Na2CO3 (200 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-99ade811df594da0bcec51dfeaa931d3
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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