Nitric Acid → Ethyl 7-nitro-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate

HRID 871268Notes

Reaction equation

HRID 871268 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=[CH:10][C:2]1=2.CC(OC(C)=O)=O.[N+:23]([O-])([OH:25])=[O:24]>CC(O)=O>[N+:23]([C:9]1[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][C:3]2[O:4][CH2:5][CH2:6][O:1][C:2]=2[CH:10]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 16648286Ethyl 2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate

Product 1

HCID 19590114Ethyl 7-nitro-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

According to the procedure described in Example 6A Step 2, to a solution of ethyl 2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate (1.42 g, 6.8 mmol) and Ac2O (3 mL), in AcOH (15 mL) was dropped fuming nitric acid (1 mL). The reacted ion was heated at 50° C. for 2 hours, to afford ethyl 7-nitro-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate as a solid (1.720 g, 99%). 1H NMR (300 MHz, CDCl3) δ 7.51 (s, 1H), 7.18 (s, 1H), 4.36 (m, 6H), 1.33 (t, 3H).

Sources & evidence

ORD record
ord-312b2627358c4deb97eb142d99d6bf13
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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