Reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[C:11](Cl)(=[O:14])[CH2:12][CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(=S)=S>[CH3:8][C:7]1[C:2]([CH3:1])=[C:3]([O:9][CH3:10])[CH:4]=[CH:5][C:6]=1[C:11](=[O:14])[CH2:12][CH3:13]Participants
Procedure
To a stirred solution of 2,3-dimethylanisole (197.0 g) and propionyl chloride (147.0 g) in carbon disulfide (700 ml) is added anhydrous aluminum chloride (232.0 g) at 5°-10° C. over a period of 1.5 hours. Stirring is continued for 2 hours under cooling and additional 3 hours at room temperature. The reaction mixture is poured onto crushed ice--concentrated hydrochloric acid with stirring. The mixture is extracted with chloroform and the chloroform solution is washed successively with water, dilute sodium bicarbonate solution and water and then dried over anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue is distilled at 121°-126° C. (1-2 mmHg) to give the title compound (255.0 g), which is crystallized from n-hexane, m.p. 39°-40° C.
Workup
- additionThe reaction mixture is poured
- customonto crushed ice
- extractionThe mixture is extracted with chloroform
- washthe chloroform solution is washed successively with water, dilute sodium bicarbonate solution and water
- dry with materialdried over anhydrous sodium sulfate
- customAfter removal of the solvent
- customby evaporation
- distillationthe residue is distilled at 121°-126° C. (1-2 mmHg)
Sources & evidence
- ORD record
- ord-e821cf1d067e446f94e7cc973f1392ee
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04528299
Linked notes
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