Hydrochloric Acid → 5-Nitro-3-vinylsalicylaldehyde

HRID 2254676Notes

Reaction equation

HRID 2254676 reaction equation
[CH2:1]=O.[Cl-].[CH:4]([C:6]1[C:7]([OH:35])=[C:8]([CH:29]=[C:30]([N+:32]([O-:34])=[O:33])[CH:31]=1)[CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5].[OH-].[Na+].Cl>O.CS(C)=O>[N+:32]([C:30]1[CH:31]=[C:6]([CH:4]=[O:5])[C:7]([OH:35])=[C:8]([CH:9]=[CH2:1])[CH:29]=1)([O-:34])=[O:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 867471163-Formyl-2-hydroxy-5-nitrobenzyltriphenylphosphonium chloride

Product 1

HCID 137252155-Nitro-3-vinylsalicylaldehydeYield 3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

A 50.1 g (1.67 moles) quantity of paraformaldehyde was dissolved in 60 ml of water with heating, and a solution of 7.04 g (14.7 mmoles) of 3-formyl-2-hydroxy-5-nitrobenzyltriphenylphosphonium chloride in 100 ml of dimethylsulfoxide was added thereto, giving a homogeneous solution. Thereafter, a 12N aqueous solution of sodium hydroxide was gradually added to the solution at room temperature and the reaction was effected for 11 hours. A 260 ml quantity of water was added to the reaction mixture and the precipitated crystals of triphenylphosphine oxide were separated by filtration. The filtrate obtained was neutralized with diluted hydrochloric acid, followed by extraction with ether. The liquid extract was concentrated and the residue was recrystallized using chloroform, giving 1.23 g (yield: 3%) of 5-nitro-3-vinylsalicylaldehyde as yellow crystals.

Workup

  1. temperaturewith heating
  2. customgiving a homogeneous solution
  3. customthe precipitated crystals of triphenylphosphine oxide were separated by filtration
  4. customThe filtrate obtained
  5. extractionfollowed by extraction with ether
  6. extractionThe liquid extract
  7. concentrationwas concentrated
  8. customthe residue was recrystallized

Sources & evidence

ORD record
ord-62b83c1c439847ac92aa49aa4340dc0f
Source dataset
uspto-grants-1993_08
Patent number
US05236958

Reaction notes

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