Acrylonitrile → 3-(2-Cyanoethoxymethyl)-2-nitrotoluene

HRID 1906140Notes

Reaction equation

HRID 1906140 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([N+:10]([O-:12])=[O:11])=[C:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1.[C:13](#[N:16])[CH:14]=[CH2:15].CC(C)([O-])C.[K+]>>[C:13]([CH2:14][CH2:15][O:1][CH2:2][C:3]1[C:4]([N+:10]([O-:12])=[O:11])=[C:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1)#[N:16]

Participants

4

Reactant 3

HCID 7855AcrylonitrileHCID 5619893-Methyl-2-nitrobenzenemethanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 202126833-(2-Cyanoethoxymethyl)-2-nitrotolueneYield 90%

Procedure

A mixture of 10 grams (g) [60 millimoles (mMol)] of 3-hydroxymethyl-2-nitrotoluene (1) (Aldrich Chemical Co., Milwaukee, WI) and 7.9 milliliters (ml) of acrylonitrile was stirred under argon at room temperature. Potassium tert-butoxide [10 milligrams (mg)] was added, followed 90 minutes later by an additional 10 mg portion. After a total of 3 hours, the reaction was quenched by the addition of 0.2 ml of acetic acid. Volatile material was removed under reduced pressure, and the residue chromatographed on 300 g of silica gel eluting with methylene chloride (CH2Cl2). Fractions of approximately 17 ml were collected. Fractions 155-200 were combined and the solvent evaporated to give 12.5 grams (g) (90% yield) of 3-(2-cyanoethoxymethyl)-2-nitrotoluene (2) as a clear oil.

Workup

  1. customAfter a total of 3 hours, the reaction was quenched by the addition of 0.2 ml of acetic acid
  2. customVolatile material was removed under reduced pressure
  3. customthe residue chromatographed on 300 g of silica gel eluting with methylene chloride (CH2Cl2)
  4. customFractions of approximately 17 ml were collected
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-19f4f3005e0043eaa6c15b8d984369bc
Source dataset
uspto-grants-1987_03
Patent number
US04650771

Reaction notes

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