beta-(p-Chlorophenyl)propionic acid → 4-(4-Chlorophenyl)butan-2-one

HRID 1366921Notes

Reaction equation

HRID 1366921 reaction equation
[CH3:1][Li].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:6][CH:5]=1>CCOCC>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12](=[O:14])[CH3:1])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 123137beta-(p-Chlorophenyl)propionic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 2192774-(4-Chlorophenyl)butan-2-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.6 M Methyl lithium (33.9 mL, 54.17 mmol) was added over 70 min to a stirring 0° C. solution of 3-(4-chlorophenyl)-propionic acid (5.0072 g, 27.08 mmol) in dry Et2O (135 mL, 0.2 M): The ice bath was removed, and the reaction was allowed to stir at room temperature overnight. The reaction was the poured into rapidly stirring ice water containing aq. HCl. The organic layer was removed, washed with NaHCO3 and brine, then dried with Na2SO4, filtered, concentrated, and purified by silica gel chromatography (Combiflash column, 98:2 to 95:5 Hexanes:EtOAc) to achieve pure 66 (2.4253 g, 49.0%): 1H (CDCl3, 400 MHz): δ 7.14 (2H, d, J=8.3 Hz), 7.03 (2H, d, J=8.3 Hz), 2.77 (2H, t, J=7.5 Hz), 2.64 (2H, t, J=7.5 Hz), 2.04 (3H, s) ppm. 13C (CDCl3, 100 MHz): δ 207.12, 139.38, 131.59, 129.55, 128.35, 44.62, 29.82, 28.78 ppm. DEPT (CDCl3, 100 MHz): CH3 carbons: 29.82; CH2 carbons: 44.62, 28.78; CH carbons: 129.55, 128.35 ppm. HPLC: 10.361 min. (Note: SM has HPLC retention time of 9.409 min.)

Workup

  1. customThe ice bath was removed
  2. additionpoured into rapidly stirring ice water containing aq. HCl
  3. customThe organic layer was removed
  4. washwashed with NaHCO3 and brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (Combiflash column, 98:2 to 95:5 Hexanes:EtOAc)
  9. custom10.361 min. (Note: SM has HPLC retention time of 9.409 min.)

Sources & evidence

ORD record
ord-8cc211b4cbae4cdca70f579d1e2e6f64
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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