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

HRID 1075328Notes

Reaction equation

HRID 1075328 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) is dissolved in absolute ethanol (125 ml). A solution of sodium sulfide monohydrate (48.3 g) and sodium bicarbonate (16.7 g) in water (75 ml) is added to the alcoholic solution. The resulting mixture is refluxed until thin layer chromatography indicates that the starting material is exhausted. The reaction mixture is then concentrated under vacuum to an oily solid. Methylene chloride is added and the mixture filtered. The methylene chloride layer is separated, dried, and is concentrated under vacuum to yield 9.3 g of a mobile orange liquid.

Workup

  1. temperatureThe resulting mixture is refluxed until thin layer chromatography
  2. concentrationThe reaction mixture is then concentrated under vacuum to an oily solid
  3. additionMethylene chloride is added
  4. filtrationthe mixture filtered
  5. customThe methylene chloride layer is separated
  6. customdried
  7. concentrationis concentrated under vacuum

Sources & evidence

ORD record
ord-3a7163fc1d6f4477bb4415d1d70220c9
Source dataset
uspto-grants-1983_07
Patent number
US04395577

Reaction notes

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