Hydrochloric Acid → 2-Chloro-1-(2-methoxyphenyl)ethan-1-ol

HRID 2180330Notes

Reaction equation

HRID 2180330 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])=[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][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])[OH:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21069202-Chloro-1-(2-methoxyphenyl)ethanoneHCID 11084032Triethylammonium formate

Product 1

HCID 224917592-Chloro-1-(2-methoxyphenyl)ethan-1-olYield 91.4%

Reagents, catalysts & solvents 2

HCID 178425932HCID 178425932, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-2′-methoxyacetophenone (186.6 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 (1.35 mg, 0.002mmol, s/c=500) in ethyl acetate (2.0ml), 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-(2′-methoxyphenyl)ethanol (170.6 mg; yield: 90.4%; optical purity: 95.2% 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-89c80c52b95f4ffdb33d29f9ed725b19
Source dataset
uspto-grants-2005_05
Patent number
US06888012B2

Reaction notes

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