Hydrochloric Acid → 1-(2,5-Dimethoxy-4-chlorophenyl)-4-cyclohexyl-1-butanone

HRID 844420Notes

Reaction equation

HRID 844420 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11])[CH2:3][CH2:2]1.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[Cl:27].Cl>C(Cl)(Cl)(Cl)Cl>[CH:4]1([CH2:7][CH2:8][CH2:9][C:10]([C:23]2[CH:24]=[C:19]([O:18][CH3:17])[C:20]([Cl:27])=[CH:21][C:22]=2[O:25][CH3:26])=[O:11])[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2467242-Chloro-1,4-dimethoxybenzeneHCID 6451240Aluminum(III) ChlorideHCID 133156254-Cyclohexylbutanoyl chloride

Product 1

HCID 226126531-(2,5-Dimethoxy-4-chlorophenyl)-4-cyclohexyl-1-butanoneYield 51.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent3×

Procedure

3.77 g of 4-cyclohexanebutyryl chloride dissolved in 10 ml of CCl4 are added to a suspension of 2.8 g of AlCl3 in 20 ml of CCl4 at +4° C. under nitrogen. 5.2 g of 2,5-dimethoxychlorobenzene in 10 ml of CCl4 are added dropwise and the mixture is then left stirring for 3 hours at RT. The reaction medium is hydrolysed with dilute HCl solution, the phases are then separated by settling and the organic phase is extracted with DCM. After drying over MgSO4, the solution is evaporated and the residue is then purified by chromatography on silica, eluting with a heptane/DCM mixture (60/40; v/v) and then with pure DCM. 3.37 g of the expected compound are obtained: m.p.=80-81° C.

Workup

  1. waitthe mixture is then left
  2. customthe phases are then separated
  3. extractionthe organic phase is extracted with DCM
  4. dry with materialAfter drying over MgSO4
  5. customthe solution is evaporated
  6. customthe residue is then purified by chromatography on silica
  7. washeluting with a heptane/DCM mixture (60/40; v/v)

Sources & evidence

ORD record
ord-ac165cf32ebe4d8f9d24d72089e56efb
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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