ChemicalBook CAS DataBase List 1,3-BENZODIOXOLE-4-CARBOXYLIC ACID

1,3-BENZODIOXOLE-4-CARBOXYLIC ACID synthesis

13synthesis methods

Product Name:1,3-BENZODIOXOLE-4-CARBOXYLIC ACID
CAS Number:5768-39-8
Molecular formula:C8H6O4
Molecular Weight:166.13

33842-16-9

5768-39-8

The general procedure for the synthesis of 1,3-benzodioxole-4-carboxylic acid from methyl benzo[d][1,3]meso-dioxole-4-carboxylate was as follows: methyl benzo[d][1,3]meso-dioxole-4-carboxylate (0.4 g, 2.22 mmol) was dissolved in methanol (8.0 mL), and 2.0 M aqueous KOH (2.2 mL) was added and stirred at room temperature. The reaction was stirred for 3 hours at room temperature. After completion of the reaction, the mixture was concentrated to about 3 mL, diluted with water (5 mL), and the pH was adjusted to ~3 with 2.0 M HCl. The precipitate was separated by filtration, washed sequentially with water and ether, and dried in vacuo to give 1,3-benzodioxole-4-carboxylic acid as a beige solid (0.38 g, 97% yield).1H NMR (400 MHz, DMSO-d6): δ = 7.28 (dd, J = 8.0, 1.2 Hz, 1H), 6.97 (dd, J = 8.0, 1.2 Hz, 1H), 6.89 (t, J = 8.0 Hz, 1H), 6.12 (s, 2H); 13C NMR (100 MHz, DMSO-d6): δ = 165.5, 148.9, 148.5, 122.9, 121.6, 113.8, 112.5, 102.1.

7797-83-3
134 suppliers
$12.00/250mg

5768-39-8
111 suppliers
$54.00/100 mg

Yield: 96%

Reaction Conditions:

with dihydrogen peroxide;potassium carbonate in methanol;water

Steps:

22 2,3-(methylenedioxy)benzoic acid
2,3-(methylenedioxy)benzoic acid A solution of 2,3-(methylenedioxy)benzaldehyde (160mg, 1.06mmol), potassium carbonate (960 mg, 6.9 mmol) and 2.4mL of hydrogen peroxide (30-32 wt.% solution in water) in 10 mL of methanol was stirred for 16 hours at room temperature. The mixture was washed with diethyl ether. The water layer was acidified with 1 N aq. HCl to pH>1, then extracted with ethyl acetate. The organic layer was dried over MgSO₄, then concentrated to give the desired product (170mg, 96%). EI-MS (m/z) 164.8 (M^-).

References:

33842-16-9
88 suppliers
$45.00/100mg

5768-39-8
111 suppliers
$54.00/100 mg

References

23158-06-7 Synthesis