Formic Acid → HCID 86652490, compound

HRID 1943553Notes

Reaction equation

HRID 1943553 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])([CH:12]2[CH2:17][CH2:16][C:15](=COC)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH:29]([OH:31])=O.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([CH:6]1[CH2:7][CH2:8][C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])([C:12]2([CH:29]=[O:31])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962Water2×HCID 14798Sodium Hydroxide2×HCID 67082453HCID 67082453, compound

Product 1

HCID 86652490HCID 86652490, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent4×

Conditions

Temperature
30 °C

Procedure

The compound (39) (8.1 g), formic acid (87%; 9.5 g) and toluene (100 ml) were mixed, and the mixture was heated under reflux for 2 hours. The reaction mixture was cooled to 30° C., and then water (100 ml) and toluene (200 ml) were added thereto and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed sequentially with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, giving a white solid. This residue was dissolved in toluene (50 ml). The solution was added to a mixture of sodium hydroxide (95%; 0.5 g) and Solmix A-11 (32 ml) which had been cooled to 7° C., and the solution obtained was stirred at 10° C. for 2 hours. Then, an aqueous 2N-sodium hydroxide solution (16 ml) was added thereto, and the mixture was stirred at 5° C. for 2 hours. The reaction mixture obtained was poured into a mixture of water (200 ml) and toluene (200 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue obtained was concentrated, purified with a fractional operation by means of column chromatography using toluene as the eluent and silica gel as the stationary phase powder and dried, giving 7.5 g of 1-[4-pentyl-(2,3-difluorophenyl)cyclohexyl]-cyclohexanecarboaldehyde (40). The yield based on the compound (39) was 97.1%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. additionmixed
  4. customhad separated into two phases of organic and
  5. extractionaqueous phases, and extraction into an organic phase
  6. customThe organic phase obtained
  7. washwashed sequentially with water
  8. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customgiving a white solid
  11. temperaturehad been cooled to 7° C.
  12. customthe solution obtained
  13. stirringthe mixture was stirred at 5° C. for 2 hours
  14. customThe reaction mixture obtained
  15. additionmixed
  16. customhad separated into two phases of organic and
  17. extractionaqueous phases, and extraction into an organic phase
  18. customThe organic phase obtained
  19. washwashed with water
  20. dry with materialdried over anhydrous magnesium sulfate
  21. distillationThen, the solvent was distilled off under reduced pressure
  22. customthe residue obtained
  23. concentrationwas concentrated
  24. custompurified with a fractional operation by means of column chromatography
  25. customdried

Sources & evidence

ORD record
ord-3b424b9042f548d78690af74a57d1a03
Source dataset
uspto-grants-2013_03
Patent number
US08394294B2

Reaction notes

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