3-Ethoxy-4-methoxybenzaldehyde → HCID 86587914, compound

HRID 2305810Notes

Reaction equation

HRID 2305810 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH:7]=O)[CH3:2].[CH3:14][CH:15]([CH3:21])[CH2:16][CH:17]([NH:19][OH:20])[CH3:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]=[N+:19]([CH:17]([CH2:16][CH:15]([CH3:21])[CH3:14])[CH3:18])[O-:20])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH3:2]

Participants

5

Reactant 3

HCID 2447283-Ethoxy-4-methoxybenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 21111947HCID 21111947, compound

Product 1

HCID 86587914HCID 86587914, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Ethoxy-4-methoxybenzaldehyde (12.0 g, 0.0666 mol) and N-(4-methylpent-2-yl)hydroxylamine (9.36 g, 0.0799 mol) were mixed into benzene (200 mL) with p-toluenesulfonic acid monohydrate (1.0 g, 5.26 mol.). The mixture was refluxed for 16 hours under an argon atmosphere with a Dean-Stark trap to remove the generated water. The solution was rotary evaporated, dissolved in ethyl acetate, washed with 5% aqueous sodium hydroxide solution, dried over magnesium sulfate, filtered and concentrated. The title compound was obtained as a white solid (17.07 g, 91.8% yield). m.p. 87.2° C. (Rf=0.31 on a silica gel plate using hexanes;EtOAc,, 1:1, v/v, as an eluant). The N-(4-methyl-2-pentyl)hydroxylamine precursor was obtained by sodium cyanoborohydride reduction of 4-methyl-2-pentanone oxime in methanol, with hydrochloric acid catalysis.

Workup

  1. temperatureThe mixture was refluxed for 16 hours under an argon atmosphere with a Dean-Stark trap
  2. customto remove the generated water
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with 5% aqueous sodium hydroxide solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bcbe02d7e2304093a824367321279dc2
Source dataset
uspto-grants-2002_08
Patent number
US06441032B1

Reaction notes

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