1,3-Dimethoxybenzene → 4-Cyclohexyl-1-(2,4-dimethoxyphenyl)butan-1-one

HRID 844419Notes

Reaction equation

HRID 844419 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH2:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][CH2:13][C:14](Cl)=[O:15])[CH2:7][CH2:6]1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1>C(Cl)(Cl)(Cl)Cl>[CH:8]1([CH2:11][CH2:12][CH2:13][C:14]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][C:21]=2[O:25][CH3:26])=[O:15])[CH2:9][CH2:10][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 90251,3-DimethoxybenzeneHCID 6451240Aluminum(III) ChlorideHCID 133156254-Cyclohexylbutanoyl chloride

Product 1

HCID 226126744-Cyclohexyl-1-(2,4-dimethoxyphenyl)butan-1-oneYield 58.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

3.53 g of AlCl3 and 5 g of 4-cyclohexanebutyryl chloride in 100 ml of CCl4 are mixed together and 5 g of 1,3-dimethoxybenzene are added dropwise, at 0° C. After stirring for 3 hours at 0° C., the entire mixture is poured onto dilute ice-cold HCl solution. The organic phase is separated out by settling and is then washed with 0.5N NaOH. After drying over MgSO4 and evaporation of the solvent, the residue is chromatographed on a column of silica H, eluting with toluene, to give 4.5 g of the expected compound in the form of an oil.

Workup

  1. additionthe entire mixture is poured onto dilute ice-cold HCl solution
  2. customThe organic phase is separated out
  3. washis then washed with 0.5N NaOH
  4. dry with materialAfter drying over MgSO4 and evaporation of the solvent
  5. customthe residue is chromatographed on a column of silica H
  6. washeluting with toluene

Sources & evidence

ORD record
ord-039853aeeb5649be8bf3dd42efafb4c4
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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