Reaktion #87594

Reaktionsgleichung

methyl 4-formyl-2-methoxybenzoate

sulphamic acid

sodium chlorite

→

desired product

Ausbeute 123.1%

3-methoxy-4-(methoxycarbonyl)benzoic acid

Ausbeute 123.1%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeExcess of solvent was removed under vacuum
2. 2
   workup.ADDITIONThe obtained residue was diluted with water and basified with saturated sodium bicarbonate solution
3. 3
   WaschenThe aqueous layer was washed with diethyl ether
4. 4
   Sonstigeto remove organic impurities
5. 5
   SonstigeThe solid obtained
6. 6
   Filtrationwas filtered
7. 7
   Sonstigesuck dried

Vorschrift

To a cold solution of methyl 4-formyl-2-methoxybenzoate (6.0 g, 7.73 mmol) in acetone (50 mL) was added aqueous sulphamic acid solution (4.5 g, 11.59 mmol) and aqueous sodium chlorite solution (4.04 g, 11.59 mmol) at 0-5° C. The reaction mixture was stirred at RT for 3-4 h. Excess of solvent was removed under vacuum. The obtained residue was diluted with water and basified with saturated sodium bicarbonate solution. The aqueous layer was washed with diethyl ether to remove organic impurities and the obtained aqueous layer was again acidified with conc. HCl. The solid obtained was filtered and suck dried to afford 2.00 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.80 (s, 3H), 3.87 (s, 3H), 7.55-7.59 (m, 2H), 7.70 (d, J=7.8 Hz, 1H), 13.37 (s, 1H); MS (m/z): 210.97 (M+H)+.

Quelle