M-Cresol → 3-Nitrobenzaldehyde

HRID 1165614Notes

Reaction equation

HRID 1165614 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1C=O)([O-:3])=[O:2].C1[C:17]([OH:18])=CC=CC=1C.C=O.S([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>O>[N+:1]([C:4]1[CH:5]=[C:8]([CH:9]=[CH:10][CH:11]=1)[CH:17]=[O:18])([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 342M-CresolHCID 712FormaldehydeHCID 111012-NitrobenzaldehydeHCID 14798Sodium HydroxideHCID 24437Sodium Sulfite

Product 1

HCID 74493-Nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

190.0 g of water-moist m-nitrobenzaldehyde (containing 163.0 g of crude nitrobenzaldehyde of the composition: 1.5% by weight of o-isomer; 2.3% by weight of p-isomer; 96.2% by weight of m-isomer) were suspended in 445 g of water and 20.0 g of an emulsifier, which was prepared by condensation of m-cresol, formaldehyde, sodium sulphite and 2-naphthol-6-sulphonic acid, were added. The suspension was heated to 60° C. and adjusted to pH 10.4 using NaOH. The mixture was subsequently heated to reflux and stirred under reflux for 30 minutes. It was then cooled to 40° C., stirred at 40° C. for 2.5 hours and filtered off with suction. The filtered material was washed with water and freshly filtered with suction. After drying, 141.7 g of m-nitrobenzaldehyde were obtained.

Workup

  1. additionwere added
  2. temperatureThe mixture was subsequently heated
  3. temperatureto reflux
  4. temperatureunder reflux for 30 minutes
  5. temperatureIt was then cooled to 40° C.
  6. stirringstirred at 40° C. for 2.5 hours
  7. filtrationfiltered off with suction
  8. washThe filtered material was washed with water
  9. filtrationfreshly filtered with suction
  10. customAfter drying

Sources & evidence

ORD record
ord-cb3142b7d3304a07a910c2a73432db3d
Source dataset
uspto-grants-1990_03
Patent number
US04910345

Reaction notes

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