1-Chloro-2,4-dimethoxybenzene → 4-Cyclohexyl-1-(5-chloro-2,4-dimethoxyphenyl)butan-1-one

HRID 844418Notes

Reaction equation

HRID 844418 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[Cl:11].[CH2:12]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22])[CH2:14][CH2:13]1>C(Cl)(Cl)(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH:15]1([CH2:18][CH2:19][CH2:20][C:21]([C:6]2[CH:5]=[C:4]([Cl:11])[C:3]([O:2][CH3:1])=[CH:8][C:7]=2[O:9][CH3:10])=[O:22])[CH2:16][CH2:17][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 1389051-Chloro-2,4-dimethoxybenzeneHCID 133156254-Cyclohexylbutanoyl chloride

Product 1

HCID 226125764-Cyclohexyl-1-(5-chloro-2,4-dimethoxyphenyl)butan-1-one

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

10 g of 2,4-dimethoxychlorobenzene and 10.93 g of 4-cyclohexanebutyryl chloride obtained in step 1 of Preparation 1.1 in 100 ml of CCl4 are mixed together at 0° C. and 6.35 ml of TiCl4 are added. After stirring for 2 hours at 0° C., the mixture is poured onto ice-cold 1N HCl solution and the organic phase is then separated out by settling and washed with 0.5N NaOH. After drying over MgSO4 and evaporation of the solvent, 20 g of the expected product are obtained.

Workup

  1. additionare mixed together at 0° C.
  2. additionthe mixture is poured onto ice-cold 1N HCl solution
  3. customthe organic phase is then separated out
  4. washwashed with 0.5N NaOH
  5. dry with materialAfter drying over MgSO4 and evaporation of the solvent, 20 g of the expected product
  6. customare obtained

Sources & evidence

ORD record
ord-853b0adaf15c4e308cf98017c60409f8
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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