Formic Acid → 4'-(4-Butoxy-2,3-difluorophenyl)-bicyclohexyl-4-one

HRID 1886721Notes

Reaction equation

HRID 1886721 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][C:15]([CH:18]3[CH2:27][CH2:26][C:21]4(OCC[O:22]4)[CH2:20][CH2:19]3)=[CH:14][CH2:13]2)=[C:8]([F:28])[C:7]=1[F:29])[CH2:2][CH2:3][CH3:4].C(O)=O.O>C1(C)C=CC=CC=1>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:13][CH2:14][CH:15]([CH:18]3[CH2:27][CH2:26][C:21](=[O:22])[CH2:20][CH2:19]3)[CH2:16][CH2:17]2)=[C:8]([F:28])[C:7]=1[F:29])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 666809238-[4-(4-Butoxy-2,3-difluorophenyl)-cyclohexenyl]-1,4-dioxaspiro[4.5]decane

Product 1

HCID 666837754'-(4-Butoxy-2,3-difluorophenyl)-bicyclohexyl-4-oneYield 98.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
30 °C

Procedure

The compound (23) (7.7 g), formic acid (87%; 8.7 g) and toluene (100 ml) were mixed and the mixture was heated to reflux for 2 hours. After the reaction mixture had been cooled to 30° C., water (200 ml) and toluene (200 ml) were added to the mixture and mixed with it. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and the extraction into an organic phase was carried out. The resulting organic phase was separated, and washed successively with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. Then the solvent was distilled off under reduced pressure, and the residue was purified by recrystallization from heptane solvent and dried to give 4′-(4-butoxy-2,3-difluorophenyl)-bicyclohexyl-4-one (24) (6.8 g). The yield based on the compound (23) was 99.0%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. additionmixed with it
  4. customhad separated into two phases of organic and aqueous phases
  5. extractionthe extraction into an organic phase
  6. customThe resulting organic phase was separated
  7. washwashed successively with water
  8. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate
  9. distillationThen the solvent was distilled off under reduced pressure
  10. customthe residue was purified by recrystallization from heptane solvent
  11. customdried

Sources & evidence

ORD record
ord-f71525002d68406798f03c48152d9988
Source dataset
uspto-grants-2013_08
Patent number
US08501038B2

Reaction notes

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