p-Toluenesulfonic acid → HCID 10947508, compound

HRID 1790564Notes

Reaction equation

HRID 1790564 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][C:15]([CH3:20])([CH2:18]O)[CH2:16][OH:17].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]1[O:17][CH2:16][C:15]([CH3:20])([CH3:18])[CH2:14][O:5]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31344Neopentyl glycolHCID 793516-Bromo-3,4-dimethoxybenzaldehyde

Product 1

HCID 10947508HCID 10947508, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.6 g of 2-bromo-4,5-dimethoxybenzaldehyde and 3.22 g of 2,2-dimethyl-1,3-propanediol were dissolved in 200 ml of toluene and boiled at reflux in the presence of 0.8 g of p-toluenesulphonic acid for 3 hrs. Then, the reaction mixture was left to cool to room temperature and was washed with NaHCO3 solution, water and saturated NaCl solution. Subsequently, the solvent was removed in a vacuum and there were obtained 5.1 g of 2-(2-bromo-4,5-dimethoxy-phenyl)-5,5-dimethyl-[1,3]dioxan as yellow-green needles.

Workup

  1. waitThen, the reaction mixture was left
  2. washwas washed with NaHCO3 solution, water and saturated NaCl solution
  3. customSubsequently, the solvent was removed in a vacuum

Sources & evidence

ORD record
ord-95c7c21a21b646cd96c5166a49adad2b
Source dataset
uspto-grants-2006_07
Patent number
US07071212B2

Reaction notes

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