Hydrochloric Acid → (5-Methyl-2-nitrophenyl)acetic acid

HRID 471992Notes

Reaction equation

HRID 471992 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:19]([O-:21])=[O:20])=[C:6]([CH:8](C(OCC)=O)[C:9]([O:11]CC)=[O:10])[CH:7]=1.Cl>C(O)(=O)C.O.CC#N>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:19]([O-:21])=[O:20])=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 11737983HCID 11737983, compound

Product 1

HCID 14740976(5-Methyl-2-nitrophenyl)acetic acidYield 84.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Diethyl 2-(5-methyl-2-nitro-phenyl)propanedioate (9.50 g, 32.2 mmol) was suspended in glacial acetic acid (40 mL) and warmed until it had dissolved. Hydrochloric acid (40 mL of 6 M solution, 240.0 mmol) was added dropwise and the solution heated at reflux for 24 h. After cooling to room temperature the reaction was diluted with water and extracted with ether. The ether was dried over Na2SO4, filtered, and concentrated in vacuo to afford a light orange solid. The solid was dissolved in minimal CH3CN and added dropwise to stirring 0.05 N HCl (300 mL) resulting in a beige precipitate. The suspension was cooled in an ice bath, filtered, and washed with water to obtain 2-(5-methyl-2-nitro-phenyl)acetic acid as a beige crystalline solid (5.30 g, 84% yield). LC/MS m/z 391.4 [M+H]+. 1H NMR (400.0 MHz, DMSO-d6) δ 12.51 (s, 1H), 8.01 (d, J=8.9 Hz, 1H), 7.36 (m, 2H), 3.95 (s, 2H), 2.40 (s, 3H).

Workup

  1. temperaturewarmed until it
  2. dissolutionhad dissolved
  3. temperaturethe solution heated
  4. temperatureat reflux for 24 h
  5. extractionextracted with ether
  6. dry with materialThe ether was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford a light orange solid
  10. additionadded dropwise
  11. customresulting in a beige precipitate
  12. temperatureThe suspension was cooled in an ice bath
  13. filtrationfiltered
  14. washwashed with water

Sources & evidence

ORD record
ord-7034fcfba5a04860968c516222ec381b
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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