Salicylaldehyde → HCID 15572710, compound

HRID 443751

Reaction equation

HRID 443751 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 6421971,4-Dichloro-2-butene, (2E)-HCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 15572710HCID 15572710, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 2 lt of refluxing water, 3 ml of 40% aqueous tetrabutylammonium hydroxide, 250 ml of salicylaldehyde and 280 ml of trans-1,4-dichloro-2-butene are added while vigorously stirring, followed by the dropwise addition of the solution of 83 g of sodium hydroxide in 400 ml of water at such a rate that the pH of the mixture is kept between 7 and 8 (ca 25 minutes). Thereafter the mixture is refluxed for about 6 minutes until the pH is about 7, cooled to 20° and the aqueous layer is extracted with diethyl ether. The extract is combined with the organic layer, washed with 5% aqueous sodium hydroxide, dried, evaporated, the residue distilled and the fraction boiling at 141°-147°/0.7 mmHg collected, to yield the 2-(4-chloro-trans-2-butenyloxy)-benzaldehyde.

Workup

  1. customis kept between 7 and 8 (ca 25 minutes)
  2. temperatureThereafter the mixture is refluxed for about 6 minutes until the pH is about 7
  3. temperaturecooled to 20°
  4. extractionthe aqueous layer is extracted with diethyl ether
  5. washwashed with 5% aqueous sodium hydroxide
  6. customdried
  7. customevaporated
  8. distillationthe residue distilled
  9. customthe fraction boiling at 141°-147°/0.7 mmHg collected

Sources & evidence

ORD record
ord-c4fd0fa19a9945cd80ce9ee3fa857981
Source dataset
uspto-grants-1981_04
Patent number
US04261907

Linked notes

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