4-Methylbenzaldehyde → HCID 19475, compound

HRID 1795031Notes

Reaction equation

HRID 1795031 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.Cl.[NH2:11][OH:12].C(N(CC)CC)C>O1CCCC1>[OH:12][N:11]=[CH:7][C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 19475HCID 19475, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-tolualdehyde (600 mg, 5 mmol) in tetrahydrofuran (3 ml) was added hydroxylamine hydrochloride (700 mg, 10 mmol) and triethylamine (1.4 ml, 10 mmol). The reaction was subjected to microwave; absorbance normal; temp: 150° C.; time; 600 (s). The solid material was filtered off, and solvent removed from the filtrate under reduced pressure. The residue was purified using column chromatography (2:1 Hexanes:Ethyl Acetate) to provide (hydroxyimino)(4-methylphenyl)methane (500 mg).

Workup

  1. custom150° C.
  2. filtrationThe solid material was filtered off
  3. customsolvent removed from the filtrate under reduced pressure
  4. customThe residue was purified

Sources & evidence

ORD record
ord-e2403eba40314a459efa44ee0e264610
Source dataset
uspto-grants-2006_04
Patent number
US07026321B2

Reaction notes

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