Formic Acid → 2-Chloro-1-(3-chloro-phenyl)-ethanol

HRID 2180328Notes

Reaction equation

HRID 2180328 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)=[O:4].C(N(CC)CC)C.C(O)=O.Cl>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.C(OCC)(=O)C>[Cl:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 168006Ethanone, 2-chloro-1-(3-chlorophenyl)-

Product 1

HCID 114695632-Chloro-1-(3-chloro-phenyl)-ethanolYield 93.4%

Reagents, catalysts & solvents 2

HCID 178425932HCID 178425932, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-3′-chloroacetophenone (945.0 mg, 5.0 mmol), triethylamine (0.73 ml, 5.25 mmol), and formic acid (0.23 ml, 5.25 mmol) were added to an ethyl acetate (5.0 ml) solution containing chloro(pentamethylcyclopentadienyl)rhodium (III) (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (1.35 mg, 0.002 mmol, s/c=5000) which was prepared in the same manner as described in Organic Letters, 1999, vol. 1, pp. 841-843, Supporting Information (see the above-described URL), and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, 1 M hydrochloric acid (5.3 ml) was added, and the reaction product was extracted with ethyl acetate (5 ml) and dried over magnesium sulfate. Evaporation of the solvent yielded a desired compound, (+)-2-chloro-1-(3′-chlorophenyl)ethanol (891.5 mg; yield: 93.4%; optical purity: 93.8% ee).

Workup

  1. customwas prepared in the same manner
  2. additionwas added
  3. extractionthe reaction product was extracted with ethyl acetate (5 ml)
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-df86eb647a4e412bbe01b7a433db1ddf
Source dataset
uspto-grants-2005_05
Patent number
US06888012B2

Reaction notes

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