반응 #344904

반응 방정식

2-methyl-1,4-dihydrobenzoic acid

polysiloxane

→

2-methylbenzoic acid

용매

hexane

decalin

반응 조건

후처리

1. 1
   workup.ADDITIONcontaining a homogeneous dispersion of metal particles (0.100 g)
2. 2
   온도The solution was heated
3. 3
   온도to reflux for 19 h
4. 4
   온도On cooling the reaction mixture
5. 5
   추출extracted with aqueous sodium hydroxide (5%) solution (2×5 mL)
6. 6
   추출extracted with chloroform (3×4 mL)
7. 7
   건조The combined organic layer was dried over anhydrous sodium sulfate
8. 8
   기타Removal of solvent
9. 9
   기타on rotary evaporator

실험 절차

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).

출처