2-propylpropane-1,3-diol → HCID 21993300, compound

HRID 1977555Notes

Reaction equation

HRID 1977555 reaction equation
[CH2:1]([CH:4]([CH2:7][OH:8])[CH2:5][OH:6])[CH2:2][CH3:3].[F:9][C:10]([F:22])([F:21])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH:19]=O)=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[CH2:1]([CH:4]1[CH2:7][O:8][CH:19]([CH2:18][CH2:17][C:14]2[CH:15]=[CH:16][C:11]([C:10]([F:9])([F:21])[F:22])=[CH:12][CH:13]=2)[O:6][CH2:5]1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 70211562-propylpropane-1,3-diolHCID 216838073-[4-(Trifluoromethyl)phenyl]propanal

Product 1

HCID 21993300HCID 21993300, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Propyl-1,3-propanediol 17.4 g (147 mol) and the above 3-(4-trifluoromethylphenyl)propanal 20.0 g (98.9 mmol) were dissolved in toluene 200 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-(2-(4-trifluoromethylphenyl)ethyl)-1,3-dioxane 10.8 g (35.7 mmol). The yield was 36.1% from 3-(4-trifluoromethylphenyl) propanal.

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-1fa9c743b41149f0ad7c0d14c1fd84d4
Source dataset
uspto-grants-2001_05
Patent number
US06235355B1

Reaction notes

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