Hydrogen Bromide → HCID 88832637, compound

HRID 917998Notes

Reaction equation

HRID 917998 reaction equation
[CH2:1]([C:3](O)([CH2:6][CH2:7][O:8][CH:9]([CH2:11][CH3:12])[CH3:10])[CH:4]=[CH2:5])[CH3:2].Br.BrCC=C(CC)CCOC(CC)C.[CH:28]1[CH:33]=[C:32]([CH:34]=[O:35])[C:31]([OH:36])=[CH:30][CH:29]=1.[OH-].[K+]>COCCOC>[CH2:1]([C:3]([CH2:6][CH2:7][O:8][CH:9]([CH2:11][CH3:12])[CH3:10])=[CH:4][CH2:5][O:36][C:31]1[CH:30]=[CH:29][CH:28]=[CH:33][C:32]=1[CH:34]=[O:35])[CH3:2]

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 6998SalicylaldehydeHCID 14797Potassium HydroxideHCID 21515992HCID 21515992, compoundHCID 88832519HCID 88832519, compound

Product 1

HCID 88832637HCID 88832637, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

9.3 g (0.05 mol) of 3-ethyl-5-sec.butoxy-1-penten-3-ol are added dropwise at 5° in the course of 15 minutes and while stirring to 20 cc of 48% hydrobromic acid. After stirring the mixture vigorously at 5° to 10° for half an hour it is extracted with ether, the ether extract is extracted with 10% soda solution and subsequently with saturated solution of sodium chloride, is dried with potassium carbonate and concentrated by evaporation. The resulting 1-bromo-3-ethyl-5-sec.butoxy-2-pentene is added without purification to 6.1 g (0.05 mol) of salicylic aldehyde and 2.8 g (0.05 mol) of potassium hydroxide in 80 cc of 1,2-dimethoxy ethane. The mixture is stirred at 20°-25° for 24 hours, is subsequently filtered and concentrated by evaporation at reduced pressure. The residue is taken up in ether, extracted with icy cold 10% sodium hydroxide solution and subsequently with saturated salt solution, is dried with sodium sulphate and evaporated.

Workup

  1. extractionis extracted with ether
  2. extractionthe ether extract
  3. extractionis extracted with 10% soda solution and subsequently with saturated solution of sodium chloride
  4. dry with materialis dried with potassium carbonate
  5. concentrationconcentrated by evaporation
  6. stirringThe mixture is stirred at 20°-25° for 24 hours
  7. filtrationis subsequently filtered
  8. concentrationconcentrated by evaporation at reduced pressure
  9. extractionextracted with icy cold 10% sodium hydroxide solution and subsequently with saturated salt solution
  10. dry with materialis dried with sodium sulphate
  11. customevaporated

Sources & evidence

ORD record
ord-4edd2ba6782b478d9c2915511f69a015
Source dataset
uspto-grants-1976_07
Patent number
US03968235

Reaction notes

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