Hydrochloric Acid → 2-Methyl-6-nitrobenzaldehyde

HRID 992820Notes

Reaction equation

HRID 992820 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[CH:4]=NO.Cl.C=[O:16].O>O1CCCC1>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[CH:4]=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 962WaterHCID 853610482-Methyl-6-nitrobenzaldoxime

Product 1

HCID 140982782-Methyl-6-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 65° C., 14 g of 2-methyl-6-nitrobenzaldoxime (80 mmol) are stirred in a mixture of 55 ml of 5% strength hydrochloric acid, 37 g of a 37% strength solution of formaldehyde, 50 ml of water and 100 ml of tetrahydrofuran for 24 hours. The phases are subsequently separated, and the dark phase is extracted with methylene chloride/water. The organic phase is dried with sodium sulfate and concentrated. This gives 10.1 g of crude product which is purified by filtration over silica gel using toluene as mobile phase.

Workup

  1. customThe phases are subsequently separated
  2. extractionthe dark phase is extracted with methylene chloride/water
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. concentrationconcentrated
  5. filtrationThis gives 10.1 g of crude product which is purified by filtration over silica gel

Sources & evidence

ORD record
ord-0aaf174442334cfdbfbe7847a7c9df02
Source dataset
uspto-grants-2002_10
Patent number
US06469176B1

Reaction notes

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