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

HRID 1029993Notes

Reaction equation

HRID 1029993 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-nitropheyl 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-3bf7c218666e4c9cb9b7629f55677f43
Source dataset
uspto-grants-1992_04
Patent number
US05104414

Reaction notes

Loading…