Hydrochloric Acid → HCID 69110726, compound

HRID 2214327Notes

Reaction equation

HRID 2214327 reaction equation
[C:1]1([C@H:7]([CH3:11])[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:12]>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3].C1(C)C=CC=CC=1>[Cl:12][C:1]1[CH:6]=[CH:5][C:4]([C:8](=[O:9])[C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:11])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 7021723HCID 7021723, compound

Product 1

HCID 69110726HCID 69110726, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 5483663Ferric acetylacetonateCatalystHCID 1140TolueneSolvent

Procedure

Into a 20 L four-necked flask (flask B), 691 g of (S)-2-phenylpropionic chloride and 4.4 L of toluene were put and cooled to −10° C. in an atmosphere of nitrogen, and 1.41 g (4.00 mmol) of iron(III) acetylacetonate was added thereto. While maintaining the reaction temperature to be at most −10° C., the Grignard reagent prepared in the flask A was dropwise added thereto over a period of 4 hours in an atmosphere of nitrogen, and the temperature was raised to room temperature after completion of the dropwise addition, followed by stirring overnight, and then the mixture was cooled to 10° C., and 4 L of diluted hydrochloric acid was added thereto. The organic phase was separated, the aqueous phase was extracted with toluene, the toluene layer and the organic phase were put together, washed with water 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=1/1), and recrystallization from ethanol was carried out to obtain 329 g (1.34 mol) of (S)-1-(4-chlorophenyl)-2-phenylpropane-1-one [H-Ph-CH(CH3)—C(O)-Ph-Cl] as white crystals (yield: 34%).

Workup

  1. additionwas added
  2. temperatureWhile maintaining the reaction temperature
  3. customto be at most −10° C.
  4. additionA was dropwise added
  5. additionafter completion of the dropwise addition
  6. temperaturethe mixture was cooled to 10° C.
  7. customThe organic phase was separated
  8. extractionthe aqueous phase was extracted with toluene
  9. washwashed with water and saturated salt solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off
  12. customto obtain a crude product
  13. customThe crude product was purified by silica gel column chromatography (developing solvent: hexane/toluene=1/1), and recrystallization from ethanol

Sources & evidence

ORD record
ord-2591efdaa0784ab59d233871f23c79a7
Source dataset
uspto-grants-2006_09
Patent number
US07108895B2

Reaction notes

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