Hydrochloric Acid → 2-Methyl-4-methoxy-5-nitrophenol

HRID 2050750Notes

Reaction equation

HRID 2050750 reaction equation
S([O:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([O:15][CH3:16])=[CH:8][C:7]=1[CH3:17])(=O)(=O)C.[OH-].[Na+].Cl>CO.O>[CH3:17][C:7]1[CH:8]=[C:9]([O:15][CH3:16])[C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=1[OH:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 198211562-Methyl-4-methoxy-5-nitrophenyl mesylate

Product 1

HCID 199401542-Methyl-4-methoxy-5-nitrophenolYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

In 110 ml of methanol was dissolved 15.5 g (59.4 mmol) of 2-methyl-4-methoxy-5-nitrophenyl mesylate. Then 6.5 g of sodium hydroxide dissolved in 20 ml of water was added thereto. The obtained mixture was heated under reflux for 1 hour. After cooling, concentrated hydrochloric acid was added to thereby acidify the mixture. Then 400 ml of water was added and crystals were precipitated. The crystals were collected by filtration and washed with water. Thus 10.9 g (59.4 mmol) of 2-methyl-4-methoxy-5-nitrophenol was obtained. The yield was 100%.

Workup

  1. additionwas added
  2. temperatureThe obtained mixture was heated
  3. temperatureunder reflux for 1 hour
  4. temperatureAfter cooling
  5. customcrystals were precipitated
  6. filtrationThe crystals were collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-f72d44e6a4f64d369075518aaaa7be56
Source dataset
uspto-grants-1991_05
Patent number
US05015260

Reaction notes

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