Salicylaldehyde → HCID 15572711, compound

HRID 1105498Notes

Reaction equation

HRID 1105498 reaction equation
[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH:19](=[O:27])[C:20]1[C:21](=[CH:23][CH:24]=[CH:25][CH:26]=1)[OH:22].[Cl:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]Cl.[OH-].[Na+]>O>[Cl:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][O:22][C:21]1[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=1[CH:19]=[O:27]

Participants

6

Reactant 4

HCID 6998SalicylaldehydeHCID 14798Sodium HydroxideHCID 2723671Tetrabutylammonium HydroxideHCID 64321151,4-Dichloro-cis-2-butene

Product 1

HCID 15572711HCID 15572711, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 1.2 lt of refluxing water, 1 ml of 40% aqueous tetrabutylammonium hydroxide, 125 ml of salicylaldehyde and 150 ml of cis-1,4-dichloro-2-butene are added while vigorously stirring, followed by the dropwise addition of the solution of 42 g of sodium hydroxide in 200 ml of water at such a rate that the pH of the mixture is kept between 7 and 8. Thereafter the mixture is refluxed until the pH is about 7, cooled and extracted with methylene chloride. The extract is washed with 5% aqueous sodium hydroxide, dried, evaporated, the residue distilled and the fraction boiling at 137°-140°/0.1 mmHg collected, to yield the 2-(4-chloro-cis-2-butenyloxy)-benzaldehyde.

Workup

  1. temperatureThereafter the mixture is refluxed until the pH is about 7
  2. temperaturecooled
  3. extractionextracted with methylene chloride
  4. washThe extract is washed with 5% aqueous sodium hydroxide
  5. customdried
  6. customevaporated
  7. distillationthe residue distilled
  8. customthe fraction boiling at 137°-140°/0.1 mmHg collected

Sources & evidence

ORD record
ord-50a045622c864a0ea7042086b11534ff
Source dataset
uspto-grants-1982_01
Patent number
US04309349

Reaction notes

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