Water → 4-Chloro-4'-methoxybutyrophenone

HRID 352046Notes

Reaction equation

HRID 352046 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>ClCCl>[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 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Anisole (6.75 g, 62.4 mmol) was dissolved in dichloromethane (80 ml). The mixture was cooled to −5° C. and aluminum chloride (8.32 g, 62.4 mmol) was added. 4-Chlorobutyryl chloride (8.8 g, 62.4 mmol) was added dropwise to the mixture at −10° C. and stirred at −10° C. for 1 hour. The reaction mixture was poured into iced water (100 ml). After separation, the organic layer was washed with 1N hydrochloric acid (50 ml), saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml), and was concentrated under reduced pressure to give 4-chloro-1-(4-methoxyphenyl)-1-butanone (12.7 g).

Workup

  1. customAfter separation
  2. washthe organic layer was washed with 1N hydrochloric acid (50 ml), saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml)
  3. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-b3da8246c80c4cc6a440dc67cf058ada
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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