Formic Acid → HCID 21993278, compound

HRID 1977564Notes

Reaction equation

HRID 1977564 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][C:9]1([C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(O)=O.O.[CH2:28]([CH:31](CO)CO)[CH2:29]C>C1(C)C=CC=CC=1>[CH2:29]([CH:5]1[CH2:4][O:3][CH:2]([CH2:7][CH2:8][C:9]2([C:15]3[CH:16]=[C:17]([F:23])[C:18]([F:22])=[C:19]([F:21])[CH:20]=3)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[O:1][CH2:6]1)[CH2:28][CH3:31]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 70211562-propylpropane-1,3-diolHCID 21993298HCID 21993298, compound

Product 1

HCID 21993278HCID 21993278, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1-(2-(1,3-Dioxane-2-yl)ethyl)cyclohexyl-3,4,5-trifluorobenzene 3.7 g (11 mmol) obtained in Example 8 and formic acid 25.0 g (540 mmol) were added to toluene 20 ml, and the mixture was refluxed with heating for 3 hours. The reactant was cooled to room temperature, water 100 ml was added, and the product was extracted with toluene. The extract was washed with water, a saturated sodium bicarbonate aqueous solution, and water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain crude 3-(4-(3,4,5-trifluorophenyl)cyclohexyl)propanal 3.5 g. The product and 2-propyl-1,3-propanediol 2.3 g (20 mmol) were dissolved in toluene 20 ml, PTS 0.5 g was added. 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 1-(2-(5-propyl-1,3-dioxane-2-yl)ethyl)cyclohexyl-3,4,5-trifluorobenzene 1.4 g (3.8 mmol). The yield was 34.5% from 1-(2-(1,3-dioxane-2-yl)ethyl)cyclohexyl-3,4,5-trifluorobenzene.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 3 hours
  3. extractionthe product was extracted with toluene
  4. washThe extract was washed with water
  5. dry with materiala saturated sodium bicarbonate aqueous solution, and water, and dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customto obtain crude 3-(4-(3,4,5-trifluorophenyl)cyclohexyl)propanal 3.5 g
  8. additionPTS 0.5 g was added
  9. temperatureThe mixture was refluxed
  10. temperaturewith heating for 3 hours
  11. customwhile removing water
  12. customformed with Dien-Stark
  13. washThe reactant was washed with a saturated sodium bicarbonate aqueous solution
  14. dry with materialwith saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  15. distillationthe solvent was distilled off
  16. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  17. customrecrystallized twice from ethanol

Sources & evidence

ORD record
ord-073ca147b0894dc6a4e1c896886a531b
Source dataset
uspto-grants-2001_05
Patent number
US06235355B1

Reaction notes

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