Acetone → HCID 58212266, compound

HRID 1095251Notes

Reaction equation

HRID 1095251 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][CH:19]([CH:22]4[CH2:27][CH2:26][C:25](=[CH:28][O:29]C)[CH2:24][CH2:23]4)[CH2:18][CH2:17]3)=[C:12]([F:31])[CH:11]=2)[CH2:6][CH2:5]1)[CH3:2].CC(C)=O.Cl.O>C1(C)C=CC=CC=1>[CH2:1]([O:3][CH:4]1[CH2:5][CH2:6][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][CH:19]([CH:22]4[CH2:27][CH2:26][CH:25]([CH:28]=[O:29])[CH2:24][CH2:23]4)[CH2:18][CH2:17]3)=[C:12]([F:31])[CH:11]=2)[CH2:8][CH2:9]1)[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 962WaterHCID 58212281HCID 58212281, compound

Product 1

HCID 58212266HCID 58212266, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

The compound (27) (7.64 g) and acetone (25 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated to 50° C. 6N-Hydrochloric acid (8 ml) was added dropwise thereto in the temperature range of 40° C. to 50° C., and the mixture was stirred for 3 hours, and cooled slowly to room temperature. Water (100 ml) and toluene (100 ml) were added and mixed thereto. 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 heptane and Solmix (heptane: Solmix=1:1 by volume), and dried, giving 2.29 g of 4′-(4-(4-ethoxycyclohexyl)-2-fluorophenyl)bi(cyclohexane)-4-carbaldehyde (28). The yield based on the compound (27) was 31.0%.

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 heptane and Solmix (heptane: Solmix=1:1 by volume)
  8. customdried

Sources & evidence

ORD record
ord-12a45ba2ce8740bfb2bdd204ff960dd5
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

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