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

HRID 2180329

Reaction equation

HRID 2180329 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 1108344-Chloro-alpha-(chloromethyl)benzenemethanolYield 90.4%

Reagents, catalysts & solvents 2

HCID 178425932HCID 178425932, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2cb9468e1afe44de9a3c891d27f21ebb
Source dataset
uspto-grants-2005_05
Patent number
US06888012B2

Linked notes

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