Hydrochloric Acid → 4-Chloro-alpha-(chloromethyl)benzenemethanol

HRID 2180329

Reaktionsgleichung

Reaktionsgleichung von HRID 2180329
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].C(O)=O.C(N(CC)CC)C.Cl>C(OCC)(=O)C.C1(C)C=CC(S(N[C@H](C2C=CC=CC=2)[C@@H](C2C=CC=CC=2)N)(=O)=O)=CC=1.Cl[Rh+]C1(C)C(C)=C(C)C(C)=C1C>[Cl:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)[OH:4]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 702982,4'-DichloroacetophenoneHCID 11084032Triethylammonium formate

Produkt 1

HCID 1108344-Chloro-alpha-(chloromethyl)benzenemethanolAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178425932HCID 178425932, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Chloro-4′-chloroacetophenone (189.6 mg, 1.0 mmol) and a formic acid/triethylamine azeotropic mixture (0.2 ml) were added to a solution of chloro(pentamethylcyclopentadienyl)rhodium (III) (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (0.67 mg, 0.001 mmol, s/c=1000) in ethyl acetate (2.0 ml), followed by stirring at room temperature for 2 hours. After completion of the reaction, 1 M hydrochloric acid (1.2 ml) was added, and the reaction product was extracted with ethyl acetate (2 ml) and dried over magnesium sulfate. Evaporation of the solvent gave a desired compound, (+)-2-chloro-1-(4′-chlorophenyl)ethanol (172.8 mg; yield: 90.2%; optical purity: 91.6% ee).

Aufarbeitung

  1. additionwas added
  2. extractionthe reaction product was extracted with ethyl acetate (2 ml)
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-2cb9468e1afe44de9a3c891d27f21ebb
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06888012B2

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