Ethyl benzo[d][1,3]dioxole-4-carboxylate synthesis

8synthesis methods

Product Name:Ethyl benzo[d][1,3]dioxole-4-carboxylate
CAS Number:23158-06-7
Molecular formula:C10H10O4
Molecular Weight:194.18

75-09-2 Synthesis

75-09-2
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3943-73-5 Synthesis

3943-73-5
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$16.00/100mg

Ethyl benzo[d][1,3]dioxole-4-carboxylate

23158-06-7
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Yield:23158-06-7 68%

Reaction Conditions:

with potassium fluoride in N,N-dimethyl-formamide at 110; for 14.5 h;

Steps:

68.2

To a solution of the compound of the previous step (22 g) in DMF (200 ml) were added potassium fluoride (36 g) and CH₂Cl₂ (9.0 ml), and the mixture was stirred at 110°C for 8 hr. CH₂Cl₂ (20 ml) was added to the solution, and the mixture was further stirred at 110°C for 6.5 hr. The reaction solution was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=4:1) to give the title compound (16 g, 68%). NMR(300MHz, CDCl₃)δ:1.39(3H, t, J=7.2Hz), 4.39(2H, q, J=7.2Hz), 6.10(2H, s), 6.86(1H, dd, J=8.1, 7.2Hz), 6.97(1H, dd, J=7.2, 1.2Hz), 7.41(1H, dd, J=8.1, 1.2Hz).

References:

EP2116538,2009,A1 Location in patent:Page/Page column 49

5768-39-8 Synthesis