反应 #344904

反应方程式

2-methyl-1,4-dihydrobenzoic acid

polysiloxane

→

2-methylbenzoic acid

溶剂

hexane

decalin

反应条件

后处理

1. 1
   workup.ADDITIONcontaining a homogeneous dispersion of metal particles (0.100 g)
2. 2
   温度The solution was heated
3. 3
   温度to reflux for 19 h
4. 4
   温度On cooling the reaction mixture
5. 5
   萃取extracted with aqueous sodium hydroxide (5%) solution (2×5 mL)
6. 6
   萃取extracted with chloroform (3×4 mL)
7. 7
   干燥The combined organic layer was dried over anhydrous sodium sulfate
8. 8
   其他Removal of solvent
9. 9
   其他on rotary evaporator

实验过程

To a suspension of 2-methyl-1,4-dihydrobenzoic acid (0.085 g, 0.05 mmol; 81% pure, from Aldrich Chemical Company) in decalin (5 mL) under a nitrogen atmosphere was added the polysiloxane matrix material containing a homogeneous dispersion of metal particles (0.100 g). The solution was heated to reflux for 19 h. On cooling the reaction mixture was diluted with hexane (25 mL) and extracted with aqueous sodium hydroxide (5%) solution (2×5 mL). The basic aqueous solution was acidified and extracted with chloroform (3×4 mL). The combined organic layer was dried over anhydrous sodium sulfate. Removal of solvent on rotary evaporator gave 2-methylbenzoic acid (0.065 g. 96%). IR(KBr) 3600-2000 (br), 2923, 1694, 1300, 920, 731 cm-1. 1H NMR (300 MHz, CDCl3) δ8..03 (ddd, J=8.5, 3.0, 1.5 Hz, 1 H), 7.42 (td, J=8.5, 1.5 Hz, 1H, 7.26 (td, J=8.5, 1.5 Hz, 1H), 7.22 (dd, J=8.5, 1.5 Hz, 1H), 2.64 (s, 3H).

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