Dichloromethane → 4-Cyclohexyl-1-(2,5-diethoxy-4-methylphenyl)butan-1-one

HRID 844421Notes

Reaction equation

HRID 844421 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Al+3].[Cl-].[Cl-].[Cl-].[CH2:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][C:21]=1[CH3:29])[CH3:18].C(Cl)Cl>C(Cl)(Cl)(Cl)Cl>[CH:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:24]2[CH:25]=[C:20]([O:19][CH2:17][CH3:18])[C:21]([CH3:29])=[CH:22][C:23]=2[O:26][CH2:27][CH3:28])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 123535631,4-Diethoxy-2-methylbenzeneHCID 133156254-Cyclohexylbutanoyl chloride

Product 1

HCID 226125564-Cyclohexyl-1-(2,5-diethoxy-4-methylphenyl)butan-1-oneYield 75.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent3×

Procedure

4 g of 4-cyclohexylbutyryl chloride dissolved in 10 ml of CCl4 are added to a suspension of 2.9 g of AlCl3 in 40 ml of CCl4 at +4° C. 4.2 g of 2,5-diethoxytoluene in 20 ml of CCl4 are added dropwise. After 4 hours at +4° C., the reaction medium is poured into dilute ice-cold HCl solution. DCM is added, the phases are separated out by settling and the organic phase is then dried over MgSO4. After evaporation of the solvent, the product is purified by chromatography on silica H, eluting with toluene. 5.33 g of the expected compound are obtained: m.p.=49-50° C.

Workup

  1. additionthe reaction medium is poured into dilute ice-cold HCl solution
  2. customthe phases are separated out
  3. dry with materialthe organic phase is then dried over MgSO4
  4. customAfter evaporation of the solvent
  5. customthe product is purified by chromatography on silica H
  6. washeluting with toluene

Sources & evidence

ORD record
ord-c1c8274ccb214c52ac9c0e02c689be9e
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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