Acetyl chloride → HCID 21219741, compound
Reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=1)[CH2:6][CH2:7][CH3:8].[Cl-].[Al+3].[Cl-].[Cl-]>O>[C:1]([C:15]1[CH:14]=[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:12]=[CH:11][C:10]=1[O:9][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
77 [ml] of acetyl chloride was added to 70.3 [g] of 1,4-di-n-butoxybenzene, 50.7 [g] of aluminum chloride was added while cooling on ice, and the reaction was carried out while stirring at -5° C. for 1 hour. The reaction liquor was poured into 1000 [ml] of water, and extracted twice with 500 [ml] methylene chloride. The extraction solution (i.e. the methylene chloride solution) was washed with water, and concentrated by evaporating off the methylene chloride as solvent under reduced pressure. Concentration of the extraction solution was continued until almost no further methylene chloride remained. The concentrated extraction solution was then subjected to chromatography on a silica gel column using a mixture of n-hexane and ethyl acetate (volume ratio of n-hexane:ethyl acetate=30:1) as eluent, and a 77.2 [g] yield of 2-acetyl-1,4-di-n-butoxybenzene was thereby obtained.
Workup
- additionwas added
- temperaturewhile cooling on ice
- extractionextracted twice with 500 [ml] methylene chloride
- washThe extraction solution (i.e. the methylene chloride solution) was washed with water
- concentrationconcentrated
- customby evaporating off the methylene chloride as solvent under reduced pressure
- extractionThe concentrated extraction solution
- additiona mixture of n-hexane and ethyl acetate (volume ratio of n-hexane:ethyl acetate=30:1) as eluent
Sources & evidence
- ORD record
- ord-d4d851ee41344f4d815183bd72bac57d
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05935756
Reaction notes
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