Nitric Acid → HCID 86631942, compound

HRID 906133Notes

Reaction equation

HRID 906133 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([CH3:16])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N+:17]([O-])([OH:19])=[O:18].S(=O)(=O)(O)O>ClCCl>[CH3:16][C:9]1[C:8]([N+:17]([O-:19])=[O:18])=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]([CH3:1])=[CH:11][C:10]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 289462Dimethyl 2,5-dimethylbenzene-1,4-dicarboxylate

Product 1

HCID 86631942HCID 86631942, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethyl 2,5-dimethylterephthalate (3.14 g, 14.1 mmol) was dissolved in dichloromethane (30 mL) and was cooled in an ice bath. Fuming nitric acid (7.6 mL) and concentrated sulfuric acid (0.92 mL) were added carefully, and the mixture was stirred for 1.75 h. The mixture was then quenched with water and diluted with dichloromethane. The aqueous portion was extracted with dichloromethane. The combined organic portion was dried over sodium sulfate, then filtered and concentrated to afford a yellow oil which was purified by column chromatography (silica gel, 10-20% ethyl acetate in hexanes) to afford dimethyl 2,5-dimethyl-3-nitroterephthalate (2.78 g, 10.4 mmol, 74% yield). 1H NMR (400 MHz, CDCl3): δ 7.85 (s, 1H), 3.94 (s, 3H), 3.89 (s, 3H), 2.49 (s, 3H), 2.46 (s, 3H); GCMS for C12H13NO6: 267 (M+).

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe mixture was then quenched with water
  3. additiondiluted with dichloromethane
  4. extractionThe aqueous portion was extracted with dichloromethane
  5. dry with materialThe combined organic portion was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow oil which
  9. customwas purified by column chromatography (silica gel, 10-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9f896387aa714fbea3aae1f45d61d411
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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