Sodium Hydroxide → HCID 86631943, compound

HRID 906134Notes

Reaction equation

HRID 906134 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([C:15]([O:17][CH3:18])=[O:16])[C:9]([CH3:19])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>O1CCOCC1.O>[CH3:18][O:17][C:15]([C:10]1[C:9]([CH3:19])=[CH:8][C:3]([C:4]([OH:6])=[O:5])=[C:2]([CH3:1])[C:11]=1[N+:12]([O-:14])=[O:13])=[O:16]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 86631942HCID 86631942, compound

Product 1

HCID 86631943HCID 86631943, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Dimethyl 2,5-dimethyl-3-nitroterephthalate (2.27 g, 8.50 mmol) was dissolved in 1,4-dioxane (20 mL) and was cooled in an ice bath. 1N Sodium hydroxide (8.5 mL) was added dropwise, and the mixture was stirred at ambient temperature for 2.25 h. Additional 1N sodium hydroxide (0.5 mL) was added drop-wise and the mixture was stirred at ambient temperature for a further 1 h at which point another 0.5 mL aliquot of 1N aqueous sodium hydroxide was added and stirring was continued for an additional 1 h. The reaction mixture was diluted with water and was washed with ether. The aqueous portion was acidified with 1N hydrochloric acid to pH ˜2 and then was extracted with ethyl acetate (2×). The combined ethyl acetate portion was dried over sodium sulfate, then filtered and concentrated to provide 4-(methoxycarbonyl)-2,5-dimethyl-3-nitrobenzoic acid (quantitative yield). 1H NMR (400 MHz, d6-DMSO): δ 13.8 (br s, 1H), 7.93 (d, 1H), 3.81 (s, 3H), 2.38 (s, 3H), 2.37 (s, 3H); MS (EI) for C11H11NO6: 252 (M−H).

Workup

  1. temperaturewas cooled in an ice bath
  2. additionwas added
  3. stirringstirring
  4. waitwas continued for an additional 1 h
  5. washwas washed with ether
  6. extractionwas extracted with ethyl acetate (2×)
  7. dry with materialThe combined ethyl acetate portion was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4bdb93dff683497b84a5f4db5b132a12
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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