Ethanol → 4-Ethoxymethyl-2,6-dimethylnitrobenzene

HRID 1577145Notes

Reaction equation

HRID 1577145 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-:12])=[O:11])=[C:5]([CH3:13])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([OH:22])[CH3:21]>>[CH2:20]([O:22][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-:12])=[O:11])=[C:5]([CH3:13])[CH:4]=1)[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 205718604-Bromomethyl-2,6-dimethylnitrobenzene

Product 1

HCID 205718654-Ethoxymethyl-2,6-dimethylnitrobenzene

Procedure

The product from Step A (19.0 g) is dissolved in ethanol (600 ml) and anhydrous potassium carbonate (32 g) is added. The reaction mixture is stirred at reflux until the reaction is complete by tlc (two hours). The mixture is cooled, and the solids are filtered, washed, and discarded. The filtrate and washings are evaporated to a residue and purified by column chromatography on silica gel, using as eluant cyclohexane/ethyl acetate (97:3 v/v). The desired product, 4-ethoxymethyl-2,6-dimethylnitrobenzene (10.4 g) is isolated as a colorless oil.

Workup

  1. temperatureat reflux until the reaction
  2. customis complete by tlc (two hours)
  3. temperatureThe mixture is cooled
  4. filtrationthe solids are filtered
  5. washwashed
  6. customThe filtrate and washings are evaporated to a residue
  7. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b7aad892e8e3499c89e4a0223508c013
Source dataset
uspto-grants-1981_09
Patent number
US04287201

Reaction notes

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