Hydrochloric Acid → HCID 19899911, compound

HRID 2110353Notes

Reaction equation

HRID 2110353 reaction equation
C[O:2][C:3](=[O:19])[CH:4]([C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])C(OC)=O.Cl>O>[F:15][C:14]1[C:9]([CH2:4][C:3]([OH:19])=[O:2])=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24824335HCID 24824335, compound

Product 1

HCID 19899911HCID 19899911, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(6-Fluoro-2-nitro-phenyl)-malonic acid dimethyl ester (12 g, 44 mmol) in a 6N aqueous solution of hydrochloric acid (200 mL) was heated at reflux for 4 hours. The mixture was cooled, diluted with 250 mL of water and extracted with diethyl ether. The ethereal layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. Crystallization from 5% ethyl acetate/hexane gave 7.6 g of (6-fluoro-2-nitro-phenyl)-acetic acid (54%). MS (ESI) m/z 200 ([M+H]+).

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with diethyl ether
  4. dry with materialThe ethereal layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customCrystallization from 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6a8a9c7d2d2841dc8698056b029a16ea
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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