反应 #4281

反应方程式

4-chlorophenylacetyl chloride

4,4,6,6-tetramethyl-1,3,5-cyclohexanetrione

Triethylamine

→

oil

2-(4'-Chlorophenylacetyl)-4,4,6,6-tetramethyl-1,3,5-cyclohexanetrione

溶剂

methylene chloride

反应条件

后处理

1. 1
   洗涤The solution was washed with 1 normal hydrochloric acid (1N HCl), 5% potassium carbonate (5% K2CO3) and saturated sodium chloride (brine)
2. 2
   干燥dried over anhydrous magnesium sulfate (MgSO4)
3. 3
   浓缩concentrated under vacuum
4. 4
   workup.DISSOLUTIONThe residue was dissolved in 15 ml acetonitrile
5. 5
   workup.ADDITIONTriethylamine (3 ml) and acetone cyanohydrin (0.3 g) were added
6. 6
   workup.STIRRINGthe mixture stirred at room temperature for 4 hours
7. 7
   洗涤After dilution with ether, the solution was washed with 1N HCl
8. 8
   萃取extracted with 5% K2CO3
9. 9
   萃取The basic extract
10. 10
    萃取extracted with ether
11. 11
    萃取The ether extract
12. 12
    洗涤was washed with brine
13. 13
    干燥dried (MgSO4)
14. 14
    浓缩concentrated under vacuum

实验过程

4-Chlorophenylacetic acid (1.7 g, 10 mmol) and oxalyl chloride (2 ml, 23 mmol) were stirred in 100 ml methylene chloride with two drops of dimethylformamide for two hours. The solvent and excess oxalyl chloride were removed under vacuum to give p-chlorophenylacetyl chloride. The 4-chlorophenylacetyl chloride and 4,4,6,6-tetramethyl-1,3,5-cyclohexanetrione (1.5 g, 8.2 mmol) were dissolved in methylene chloride. Triethylamine (3 ml) was added and the resulting solution stirred at room temperature for 30 minutes. The solution was washed with 1 normal hydrochloric acid (1N HCl), 5% potassium carbonate (5% K2CO3) and saturated sodium chloride (brine), dried over anhydrous magnesium sulfate (MgSO4) and concentrated under vacuum. The residue was dissolved in 15 ml acetonitrile. Triethylamine (3 ml) and acetone cyanohydrin (0.3 g) were added and the mixture stirred at room temperature for 4 hours. After dilution with ether, the solution was washed with 1N HCl and extracted with 5% K2CO3. The basic extract was acidified with hydrochloric acid and extracted with ether. The ether extract was washed with brine, dried (MgSO4) and concentrated under vacuum yielding 1.0 g of an oil that solidified on standing (m.p. 57°-61° C.). It was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

来源