HCID 59815092, compound → HCID 13496998, compound

HRID 250517Notes

Reaction equation

HRID 250517 reaction equation
[CH2:1]([CH:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:15][C:12]1[CH:13]=[CH:14][C:9]([C:7](=[O:8])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 59815092HCID 59815092, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 13496998HCID 13496998, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of α-hexyl-4-methyl-benzenemethanol (2.10 g, 10.2 mmol.) in anhydrous dichloromethane (45 mL) under an atmosphere of dry nitrogen was added pyridinium chlorochromate (3.08 g, 14.3 mmol., 1.4 eq.). Stirring was continued at room temperature for 3 hours after which time analysis by thin layer chromatography revealed complete conversion of the starting alcohol. Following evaporation of the reaction solvent the desired ketone (1.929 g, 93%) was isolated by flash chromatography on silica gel, eluting with hexane-ethyl acetate (4:1). 1H nmr (200 MHz, CDCl3) 0.86-1.76 (m, 3H, (CH2)5CH3), 2.41 (s, 3H, ArCH3), 2.93 (t, J=3.6 Hz, 2H, COCH2), 7.25 (d, J=4.2 Hz, 2H, 2×ArH), 7.86 (d, J=4.2 Hz, 2H, 2×ArH).

Workup

  1. customevaporation of the reaction solvent the desired ketone (1.929 g, 93%)
  2. customwas isolated by flash chromatography on silica gel
  3. washeluting with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-db1bce4983ec4c849673be0192adbb04
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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