Water → 4-Chloro-4'-methoxybutyrophenone

HRID 352047Notes

Reaction equation

HRID 352047 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18].O>C1(C)C=CC=CC=1>[Cl:13][CH2:14][CH2:15][CH2:16][C:17]([C:4]1[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=1)=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7519AnisoleHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 964144-Chloro-4'-methoxybutyrophenoneYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-10 °C

Procedure

Anisole (2.16 g, 20 mmol) was dissolved in toluene (20 ml). The mixture was cooled to −10° C. and aluminum chloride (2.67 g, 20 mmol) was added. 4-Chlorobutyryl chloride (2.47 ml, 22 mmol) was added dropwise at −10° C. and stirred for 0.5 hour at −10° C. The reaction mixture was poured into iced water (40 ml). After separation, the organic layer was washed with 20%citric acid (10 ml) twice, 1N-sodium hydroxide (10 ml) and 20% brine (10 ml) twice, and was concentrated under reduced pressure to give 4-chloro-1-(4-methoxyphenyl)-1-butanone (4.21 g, yield 99%).

Workup

  1. customAfter separation
  2. washthe organic layer was washed with 20%citric acid (10 ml) twice
  3. concentration1N-sodium hydroxide (10 ml) and 20% brine (10 ml) twice, and was concentrated under reduced pressure

Sources & evidence

ORD record
ord-754aa093e25c464d93088ec67702b288
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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