Hydrochloric Acid → 4-Ethoxymethyl-2,6-dimethylaniline

HRID 1577146Notes

Reaction equation

HRID 1577146 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-])=O)=[C:7]([CH3:15])[CH:6]=1)[CH3:2].Cl>C(O)C.[Fe]>[CH2:1]([O:3][CH2:4][C:5]1[CH:6]=[C:7]([CH3:15])[C:8]([NH2:12])=[C:9]([CH3:11])[CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 205718654-Ethoxymethyl-2,6-dimethylnitrobenzene

Product 1

HCID 205718594-Ethoxymethyl-2,6-dimethylaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product from Step B (10.0 g) in 50% aqueous ethanol (150 ml) is added iron powder (7.5 g) and concentrated hydrochloric acid (2.0 ml in 10 ml ethanol). The mixture is stirred mechanically at reflux for 2 hours. The solids are filtered hot, washed with ethanol and discarded. The filtrate is neutralized with sodium bicarbonate, evaporated to a residue and extracted with dichloromethane. The organic phase is treated with charcoal and a small amount of silica gel, dried, and evaporated to afford crude, syrupy 4-ethoxymethyl-2,6-dimethylaniline. The product could be purified further by silica gel chromatography [cyclohexane/ethyl acetate (19:1)] or used directly in the next step. Yield after chromatography is 4.8 g.

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solids are filtered hot
  3. washwashed with ethanol
  4. customevaporated to a residue
  5. extractionextracted with dichloromethane
  6. additionThe organic phase is treated with charcoal
  7. customa small amount of silica gel, dried
  8. customevaporated

Sources & evidence

ORD record
ord-7cfe412565e2475d9a7b180f603cced2
Source dataset
uspto-grants-1981_09
Patent number
US04287201

Reaction notes

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