2-propylpropane-1,3-diol → 5-Propyl-2-(4-(4-trifluoromethylphenyl)butyl)-1,3-dioxane

HRID 1977557Notes

Reaction equation

HRID 1977557 reaction equation
[CH2:1]([CH:4]([CH2:7][OH:8])[CH2:5][OH:6])[CH2:2][CH3:3].[F:9][C:10]([F:24])([F:23])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=O)=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[CH2:1]([CH:4]1[CH2:7][O:8][CH:21]([CH2:20][CH2:19][CH2:18][CH2:17][C:14]2[CH:13]=[CH:12][C:11]([C:10]([F:9])([F:23])[F:24])=[CH:16][CH:15]=2)[O:6][CH2:5]1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 70211562-propylpropane-1,3-diolHCID 137181405-(4-Trifluoromethylphenyl)pentanal

Product 1

HCID 219932875-Propyl-2-(4-(4-trifluoromethylphenyl)butyl)-1,3-dioxaneYield 51.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Propyl-1,3-propanediol 5.90 g (49.9 mmol) and the above 5-(4-trifluoromethylphenyl)pentanal 7.50 g (32.6 mmol) were dissolved in toluene 70 ml, and PTS 1 g was added, and the mixture was refluxed with heating for 3 hours while removing water formed with Dien-Stark. The reactant was washed with a saturated sodium bicarbonate aqueous solution, and then with saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: toluene), and recrystallized twice from ethanol to obtain 5-propyl-2-(4-(4-trifluoromethylphenyl)butyl)-1,3-dioxane 5.55 g (16.7 mmol). The yield was 51.2% from 5-(4-trifluoromethylphenyl) pentanal.

Workup

  1. additionPTS 1 g was added
  2. temperaturethe mixture was refluxed
  3. temperaturewith heating for 3 hours
  4. customwhile removing water
  5. customformed with Dien-Stark
  6. washThe reactant was washed with a saturated sodium bicarbonate aqueous solution
  7. dry with materialwith saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  10. customrecrystallized twice from ethanol

Sources & evidence

ORD record
ord-2b1bf185d28b464bba5a0bab47d984bf
Source dataset
uspto-grants-2001_05
Patent number
US06235355B1

Reaction notes

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