HCID 346420, compound → 1-(2-chlorophenyl)-2-methylpropan-1-one

HRID 874730Notes

Reaction equation

HRID 874730 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:12])[CH:9]([CH3:11])[CH3:10].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:12])[CH:9]([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 346420HCID 346420, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 2224231-(2-chlorophenyl)-2-methylpropan-1-oneYield 83.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-(2-chlorophenyl)-2-methylpropan-1-ol (1.5 g in 15 mL DCM) was added is to a suspension of PCC (2.62 g in 30 mL DCM) at 25° C., monitoring the reaction by TLC. After 2 h, Et2O (120 mL) was added and the reaction mixture was stirred for 15 min. The supernatant was decanted, dried (Na2SO4) and concentrated under vacuum. Purification by flash chromatography (SiO2, 0-10% EtOAc in hexanes) gave the title compound as a clear colorless oil (1.24 g, 82%). 1H NMR (400 MHz, CDCl3) δ ppm 7.41-7.27 (m, 4H), 3.37-3.30 (m, 1H), 1.19 (d, J=6.8 Hz, 6H).

Workup

  1. customthe reaction by TLC
  2. customThe supernatant was decanted
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under vacuum
  5. customPurification by flash chromatography (SiO2, 0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5e6f6f3dc08c47c48abf8bb2b42c394d
Source dataset
uspto-grants-2015_03
Patent number
US08980934B2

Reaction notes

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