Hydrochloric Acid → 4-Methoxy-3-nitrophenol

HRID 268265Notes

Reaction equation

HRID 268265 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)(=O)C.[OH-].[Na+].Cl>O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][C:7]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15676975Phenol, 4-methoxy-3-nitro-, 1-acetate

Product 1

HCID 149589074-Methoxy-3-nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 61 g. (0.29 m.) of 4-methoxy-3-nitrophenyl acetate (part B) and 34.68 g. (0.87 g. (0.87 m.) of NaOH in 500 ml. of H2O was stirred and heated on a steam bath for 2 hours. The reaction solution was acidified with 87 ml. of conc. HCl, keeping the temperature below 20°C. The acid solution was extracted three times using a total of 1500 ml. of benzene. The combined benzene extracts were dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 33 g. m.p. 78°-80°.

Workup

  1. additionA mixture of 61 g
  2. temperatureheated on a steam bath for 2 hours
  3. customthe temperature below 20°C
  4. extractionThe acid solution was extracted three times
  5. dry with materialThe combined benzene extracts were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give 33 g

Sources & evidence

ORD record
ord-85f59f56e32b42a19dce9bb6b3449877
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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