Acetic Acid → HCID 18399674, compound

HRID 1018950Notes

Reaction equation

HRID 1018950 reaction equation
C1O[C:8]2[CH:7]=[CH:6][C:5]([Br:10])=[CH:4][C:3]=2O1.[N+:11]([O-:14])(O)=[O:12].[C:15]([OH:18])(=[O:17])C>>[CH2:15]1[O:18][C:3]2[CH:8]=[CH:7][C:6]([N+:11]([O-:14])=[O:12])=[C:5]([Br:10])[C:4]=2[O:17]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 758311-Bromo-3,4-(methylenedioxy)benzene

Product 1

HCID 18399674HCID 18399674, compoundYield 90%

Conditions

Temperature
10 °C

Procedure

3,4-Methylenedioxy-bromobenzene (5 g, 23 mmol) was slowly added to a stirred solution of 35ml concentrated nitric acid and 105 ml glacial acetic acid maintained at 10° C. The reaction mixture was stirred at 15° C. for 1 h and then diluted with 200 ml ice cold water. The resulting mixture was extracted twice with 200 ml portions of ether. The combined organic phase was dried and evaporated in vacuo to give the crude product. The crude product was recrystallized from ethanol to give bright yellow needle shaped crystals of the nitro compound in 90% yield; mp 87-89° C.; IR(KBr) 1528, 1333; 1H NMR (CDCl3) δ6.14(2H,s), 7.12(1H, s), 7.45(1H, s); 13C NMR(CDCl3) δ104.0, 107.0, 109.0,114.3, 146.2, 148.0, 152.1; HRMS calcd for C3H4BrNO4: 244.9323; found: 244.9324.

Workup

  1. extractionThe resulting mixture was extracted twice with 200 ml portions of ether
  2. customThe combined organic phase was dried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-0237d2e686004cc090a31e6eca4c01c0
Source dataset
uspto-grants-2002_11
Patent number
US06486167B1

Reaction notes

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