2,6-Dichlorophenylacetone → 1175301-17-3

HRID 912038Notes

Reaction equation

HRID 912038 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10](=[O:12])[CH3:11].[BH4-].[Na+]>CO.CCCCCC.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH:10]([OH:12])[CH3:11]

Participants

5

Reactant 2

HCID 27341032,6-DichlorophenylacetoneHCID 4311764Sodium borohydride

Product 1

HCID 578123651175301-17-3

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

General Procedure GG: To a solution of 2,6-dichlorophenylacetone (500.00 mg, 2.46 mmol) in MeOH (5.0 mL) was added sodium borohydride (112 mg, 2.96 mmol) in small portions. The reaction mixture was allowed to stir overnight at rt. The reaction was monitored by TLC analysis on silica gel plates using Hexane/EtOAc (70:30) as eluent. The reaction mixture was quenched with aq. sat. NH4Cl (15 mL) and extracted with EtOAc (50 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4, and filtered. The solvent was removed under reduced pressure to give a colorless oil. The crude material was purified by silica gel chromatography using Hexane/EtOAc (70:30) as eluent to obtain the desired product as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ=1.33 (d, J=6.1 Hz, 3H), 1.49 (d, J=5.3 Hz, 1H), 3.08-3.22 (m, 2H), 4.18-4.29 (m, 1H), 7.09-7.14 (m, 1H), 7.31 (s, 1H), 7.33 (s, 1H).

Workup

  1. customThe reaction mixture was quenched with aq. sat. NH4Cl (15 mL)
  2. extractionextracted with EtOAc (50 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customto give a colorless oil
  8. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-32162da90fa440c2a02b77f1eaf99cf6
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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