Sodium Bicarbonate → 3-(Methoxymethyl)-4-methylaniline

HRID 261288Notes

Reaction equation

HRID 261288 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:3]=1[CH2:4][O:5][CH3:6].O.[S-2].[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(O)C.O>[CH3:6][O:5][CH2:4][C:3]1[CH:7]=[C:8]([CH:9]=[CH:10][C:2]=1[CH3:1])[NH2:11]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 12767666Methyl 2-methyl-5-nitrobenzyl etherHCID 19906495Sodium sulfide monohydrate

Product 1

HCID 127676673-(Methoxymethyl)-4-methylanilineYield 96.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Methyl 2-methyl-5-nitrobenzyl ether (11.5 g) was dissolved in 125 ml of absolute ethanol. To this was added a solution of sodium sulfide monohydrate (48.3 g) and sodium bicarbonate (16.7 g) in 75 ml of water. The resulting mixture was refluxed until tlc indicated all the starting material was gone. The mixture was then concentrated in vacuo to an oily solid. Methylene chloride was added and the mixture filtered. The methylene chloride layer was separated and dried. After removal of the drying agent, the solvent was concentrated in vacuo to give 9.3 g of a mobile orange liquid.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. concentrationThe mixture was then concentrated in vacuo to an oily solid
  3. additionMethylene chloride was added
  4. filtrationthe mixture filtered
  5. customThe methylene chloride layer was separated
  6. customdried
  7. customAfter removal of the drying agent
  8. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-edcb9176ca00473e94e69a8f9a2a1510
Source dataset
uspto-grants-1979_08
Patent number
US04165231

Reaction notes

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