Methanol → Benzoic acid, 4-[2-(methoxycarbonyl)phenoxy]-3-nitro-, methyl ester

HRID 1907775Notes

Reaction equation

HRID 1907775 reaction equation
OS(O)(=O)=O.[CH3:6][O:7][C:8]([C:10]1[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=1[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[N+:22]([O-:24])=[O:23])=[O:9].[CH3:29]O>>[CH3:6][O:7][C:8]([C:10]1[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=1[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O:19][CH3:29])=[O:18])=[CH:15][C:14]=1[N+:22]([O-:24])=[O:23])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 59737373HCID 59737373, compound

Product 1

HCID 59737546Benzoic acid, 4-[2-(methoxycarbonyl)phenoxy]-3-nitro-, methyl esterYield 79%

Conditions

Temperature
60 °C

Procedure

Concentrated H2SO4 (3 mL) was added to a solution of compound 545 (7.5 g, 23.64 mmol) in MeOH (80 mL) and stirred at 60° C. for 16 h. MeOH was removed under vacuum and the crude product was dissolved in AcOEt and washed with water. The organic layer was separated, dried with Na2SO4, filtered and concentrated via rotary evaporation to afford the title compound 546 (6.2 g, 79%) as a light yellow solid.

Workup

  1. customMeOH was removed under vacuum
  2. dissolutionthe crude product was dissolved in AcOEt
  3. washwashed with water
  4. customThe organic layer was separated
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-dc154489f9f64671ac3297acb43aac00
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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