Water → HCID 178448132, compound

HRID 2214328

Reaction equation

HRID 2214328 reaction equation
[C:1]1([C@H:7]([CH3:18])[CH2:8]C2C=CC(C(Cl)=O)=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([CH2:33][CH2:34][CH3:35])[CH2:29][CH2:28]1.N1C=CC=CC=1.[OH2:42]>>[CH2:33]([C@H:30]1[CH2:31][CH2:32][C@H:27]([O:26][C:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:8][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:18])=[O:42])[CH2:28][CH2:29]1)[CH2:34][CH3:35]

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 1140TolueneHCID 86591923(R)-4-(2-phenylpropyl)benzoyl chlorideHCID 178448131HCID 178448131, compound

Product 1

HCID 178448132HCID 178448132, compoundYield 75%

Procedure

Into a 200 mL eggplant-type flask, 20.0 g (83.2 mmol) of (R)-4-(2-phenylpropyl)benzoic acid obtained in third step, 80 mL of tetrachloroethylene and 19.8 g (166 mmol) of thionyl chloride were added, followed by stirring at 70° C. for 3 hours, and excess of thionyl chloride and tetrachloroethylene were distilled off under reduced pressure to obtain 22.0 g of (R)-4-(2-phenylpropyl)benzoyl chloride [H-Ph-CH(CH3)—CH2-Ph-COCl]. Then, to a 200 mL four-necked flask, 22.0 g of (R)-4-(2-phenylpropyl)benzoyl chloride, 103 mL of toluene, 11.8 g (83.2 mmol) of trans-1-hydroxy-4-propylcyclohexane and 7.90 g (99.9 mmol) of pyridine were added, followed by stirring at room temperature overnight. Water was added to the reaction solution to separate the organic phase, the aqueous phase was extracted with toluene, and the toluene layer and the organic phase were put together and washed with diluted hydrochloric acid, a sodium hydrogen carbonate aqueous solution and saturated salt solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain a crude product. The crude product was purified by silica gel column chromatography (developing solvent: hexane/toluene=3/1), and recrystallization from ethanol was carried out to obtain 22.7 g (62.4 mmol) of (R)-1-[(trans-4-propylcyclohexyloxycarbonyl)phenyl]- 2-phenylpropane [H-Ph-CH(CH3)—CH2-Ph-C(O)O-Cy-C3H7] as white crystals (yield: 75%).

Workup

  1. customto separate the organic phase
  2. extractionthe aqueous phase was extracted with toluene
  3. washwashed with diluted hydrochloric acid
  4. dry with materiala sodium hydrogen carbonate aqueous solution and saturated salt solution and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customto obtain a crude product
  7. customThe crude product was purified by silica gel column chromatography (developing solvent: hexane/toluene=3/1), and recrystallization from ethanol

Sources & evidence

ORD record
ord-576ed8583e1a4c4aa8e8af494a3bc026
Source dataset
uspto-grants-2006_09
Patent number
US07108895B2

Linked notes

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