Acetone → HCID 58212265, compound

HRID 1095239Notes

Reaction equation

HRID 1095239 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[C:19]1(C2CCC(=COC)CC2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[CH3:34][C:35]([CH3:37])=O.Cl.[OH2:39]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[CH:19]1[CH2:20][CH2:21][CH:22]([CH:2]2[CH2:7][CH2:37][CH:35]([CH:34]=[O:39])[CH2:4][CH2:3]2)[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 962WaterHCID 131729504HCID 131729504, compound

Product 1

HCID 58212265HCID 58212265, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

The compound (8) (23.28 g) and acetone (350 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated to 50° C. 6N-Hydrochloric acid (150 ml) was added dropwise thereto in the temperature range of 40° C. to 50° C., and the mixture was stirred for 3 hours, and then cooled slowly to room temperature. Water (700 ml) and toluene (700 ml) were added and mixed thereto. Then, the mixture was allowed to stand until it had separated into two phases, the organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure, and the residue was purified by means of recrystallization from a mixed solvent of toluene and heptane (toluene: heptane=1:1 by volume), and dried, giving 18.33 g of 4′-[2-fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-bicyclohexyl-4-carbaldehyde (9). The yield based on the compound (8) was 81.3%.

Workup

  1. temperaturecooled slowly to room temperature
  2. additionmixed
  3. customhad separated into two phases
  4. washwashed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customthe residue was purified by means of recrystallization from a mixed solvent of toluene and heptane (toluene: heptane=1:1 by volume)
  8. customdried

Sources & evidence

ORD record
ord-a8ecb9e49f97404eb8f53a98ca4a5ce9
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

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