Hydrochloric Acid → 3,5-Dimethoxy-4-nitrophenylacetic acid

HRID 1357865Notes

Reaction equation

HRID 1357865 reaction equation
F[C:2]1[CH:3]=[C:4]([CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[CH:5]=[C:6](F)[C:7]=1[N+:8]([O-:10])=[O:9].[CH3:20][O-:21].[Na+].Cl.[CH3:24][OH:25]>>[CH3:20][O:21][C:6]1[CH:5]=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:3]=[C:2]([O:25][CH3:24])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 10942334Sodium MethoxideHCID 18188101t-Butyl 3,5-difluoro4-nitrophenylacetate

Product 1

HCID 181881093,5-Dimethoxy-4-nitrophenylacetic acid

Procedure

A stirred solution of t-butyl 3,5-difluoro-4-nitrophenylacetate (4.5 g, Reference Example 14) in methanol (350 mL) was treated with sodium methoxide in methanol (36 g, 25 wt %) and then heated at reflux for 18 hours. The cooled reaction mixture was carefully acidified to pH 2 by addition of dilute hydrochloric acid and then partially evaporated to remove the methanol. The aqueous residue was extracted twice with ethyl acetate. The combined extracts were extracted into saturated sodium bicarbonate solution. The aqueous extract was acidified to pH 2 and extracted with twice with ethyl acetate, then dried and then evaporated to give the title compound (1.4 g) as a brown solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. customThe cooled reaction mixture
  4. custompartially evaporated
  5. customto remove the methanol
  6. extractionThe aqueous residue was extracted twice with ethyl acetate
  7. extractionThe combined extracts were extracted into saturated sodium bicarbonate solution
  8. extractionThe aqueous extract
  9. extractionextracted with twice with ethyl acetate
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-cc03761e15514c8d91b70084e96efece
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

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