p-Toluenesulfonic acid → 2-(3,5-Difluorophenyl)-5-propyl-1,3-dioxane

HRID 342326Notes

Reaction equation

HRID 342326 reaction equation
[CH2:1]([CH:4]([CH2:7][OH:8])[CH2:5][OH:6])[CH2:2][CH3:3].[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([F:18])[CH:17]=1)[CH:13]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([CH:4]1[CH2:7][O:8][CH:13]([C:12]2[CH:11]=[C:10]([F:9])[CH:17]=[C:16]([F:18])[CH:15]=2)[O:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acid2×HCID 5881603,5-DifluorobenzaldehydeHCID 70211562-propylpropane-1,3-diol

Product 1

HCID 219971532-(3,5-Difluorophenyl)-5-propyl-1,3-dioxaneYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Propyl-1,3-propanediol (83.2 g; 704 mmol) and 3,5-difluorobenzaldehyde (100 g; 704 mmol) were dissolved in toluene (1 liter), and p-toluenesulfonic acid (hereinafter referred to as PTS; 5 g) was added. The mixture was refluxed for 3 hours while being dehydrated with a Dean-Stark's device. The resultant reaction mixture was washed sequentially with saturated sodium bicarbonate solution and saturated brine and dried over magnesium sulfate. Subsequently, the solvent was evaporated. The residue was recrystallized twice from heptane, to thereby obtain 82.0 g (338 mmol) of 5-propyl-2-(3,5-difluorophenyl)-1,3-dioxane. The yield of the compound from 3,5-difluorobenzaldehyde was 48.0%.

Workup

  1. addition5 g) was added
  2. temperatureThe mixture was refluxed for 3 hours
  3. customThe resultant reaction mixture
  4. washwas washed sequentially with saturated sodium bicarbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customSubsequently, the solvent was evaporated
  7. customThe residue was recrystallized twice from heptane

Sources & evidence

ORD record
ord-e19b82bf089f4556bacf9435ba2c9c7d
Source dataset
uspto-grants-1999_01
Patent number
US05858272

Reaction notes

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