Methanol → HCID 19010167, compound

HRID 1741543Notes

Reaction equation

HRID 1741543 reaction equation
CO.[CH2:3]([O:10][C:11]1[C:16]([N+:17]([O-])=[O:18])=[CH:15][C:14]([OH:20])=[C:13]([CH3:21])[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[K+].S(OC)(O[CH3:28])(=O)=O>O>[CH2:3]([O:10][C:11]1[C:16]([N:17]=[O:18])=[CH:15][C:14]([O:20][CH3:28])=[C:13]([CH3:21])[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 19010155HCID 19010155, compound

Product 1

HCID 19010167HCID 19010167, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 ml of methanol, there were added 24.6 g (95.0 mmol) of 4-benzyloxy-2-methyl-5-nitrophenol and 6.38 g (114 mmol) of potassium hydroxide and heated under reflux. To the obtained solution, there was added 14.4 g (114 mmol) of dimethyl sulfate and heated under reflux for additional one hour. After cooling and adding 200 ml of water, the crystals thus precipitated were filtered and recrystallized from hexane-acetone (2:1 (v:v)). Thus 13.0 g (47.5 mmol) of 4-benzyloxy-2-methyl-5-nitrosoanisole was obtained as yellow crystals. The yield was 50%.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperatureheated
  4. temperatureunder reflux for additional one hour
  5. temperatureAfter cooling
  6. customthe crystals thus precipitated
  7. filtrationwere filtered
  8. customrecrystallized from hexane-acetone (2:1 (v:v))

Sources & evidence

ORD record
ord-250b866e0f5147e0b80d40e9f62706f7
Source dataset
uspto-grants-1994_08
Patent number
US05334225

Reaction notes

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