반응 #42141

반응 방정식

4-formyl-3-methoxybenzoic acid methyl ester

water

2-methyl-2-butene

NaClO2

→

title intermediate

수율 47.0%

2-Methoxyterephthalic Acid 4-Methyl Ester

수율 47.0%

용매

DCM

tert-butyl alcohol

반응 조건

후처리

1. 1
   기타The solvent was then removed under reduced pressure
2. 2
   기타The crude reaction mixture
3. 3
   추출the product was extracted with 1N NaOH (200 mL)
4. 4
   세척The aqueous layer was washed with DCM (200 mL)
5. 5
   추출the product extracted with DCM (200 mL)
6. 6
   세척The organic layer was then washed with water (100 mL), NaCl (sat.) (100 mL)
7. 7
   건조dried over MgSO4
8. 8
   여과filtered
9. 9
   기타The solvent was removed under reduced pressure
10. 10
    기타to use without further purification

실험 절차

To a stirred solution of 4-formyl-3-methoxybenzoic acid methyl ester (5.0 g, 26 mmol; prepared as described in Preparation 17) in tert-butyl alcohol (200 mL) was added NaH2PO4-2H2O (3.6 g, 26 mmol), water (50 mL), 2-methyl-2-butene (11 mL, 104 mmol), and finally NaClO2 (7.02 g, 78 mmol). The reaction was allowed to stir at room temperature for 4 hours. The solvent was then removed under reduced pressure. The crude reaction mixture was then dissolved in DCM (200 mL) and the product was extracted with 1N NaOH (200 mL). The aqueous layer was washed with DCM (200 mL) and then neutralized with 6N HCl (˜40 mL) and the product extracted with DCM (200 mL). The organic layer was then washed with water (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was sufficiently pure to use without further purification. The title intermediate was obtained in 47% yield (2.4 g, 12.3 mmol).

출처