Hydrochloric Acid → 2-(3-Hydroxy-4-nitrophenyl)acetic acid

HRID 1372559Notes

Reaction equation

HRID 1372559 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:18](C(OCC)=O)[C:19]([O:21]CC)=[O:20])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])C1C=CC=CC=1.Cl>C(O)(=O)C>[OH:8][C:9]1[CH:10]=[C:11]([CH2:18][C:19]([OH:21])=[O:20])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58778826HCID 58778826, compound

Product 1

HCID 235083252-(3-Hydroxy-4-nitrophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of diethyl 3-benzyloxy-4-nitrophenylmalonate (22.0 g, 57.8 mmol), acetic acid (200 ml) and concentrated hydrochloric acid (100 ml) was heated under reflux for 15 hours under stirring. After the reaction mixture was cooled to room temperature, the solvent was distilled off from the reaction mixture under reduced pressure. The solid thus obtained was collected by filtration under reduced pressure, followed by drying under reduced pressure, whereby the title compound (5.45 g, 48%) was obtained as a pale yellow amorphous substance.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. distillationthe solvent was distilled off from the reaction mixture under reduced pressure
  4. customThe solid thus obtained
  5. filtrationwas collected by filtration under reduced pressure
  6. dry with materialby drying under reduced pressure, whereby the title compound (5.45 g, 48%)
  7. customwas obtained as a pale yellow amorphous substance

Sources & evidence

ORD record
ord-c814f04f5adc44f5a40975f2396b2adc
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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