Hydrochloric Acid → 2-Methyl-6-nitrobenzaldehyde

HRID 970163Notes

Reaction equation

HRID 970163 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 37% strength formaldehyde solution, 50 ml of water and 100 ml of tetrahydrofuran for 24 hours. The phases are then 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 through silica gel using the mobile phase toluene.

Workup

  1. customThe phases are then 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 through silica gel using the mobile phase toluene

Sources & evidence

ORD record
ord-d5d12dbe55e542d2818b98584b9c55e1
Source dataset
uspto-grants-2007_12
Patent number
US07309802B2

Reaction notes

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