Sodium Hydroxide → 5,5-Dibromo-2-(propan-2-yl)pent-4-enoic acid

HRID 647555Notes

Reaction equation

HRID 647555 reaction equation
[OH-].[Na+].[Br:3][C:4]([Br:16])=[CH:5][CH2:6][CH:7]([CH:13]([CH3:15])[CH3:14])[C:8]([O:10]CC)=[O:9]>O.C(O)C>[Br:3][C:4]([Br:16])=[CH:5][CH2:6][CH:7]([CH:13]([CH3:14])[CH3:15])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13246111HCID 13246111, compound

Product 1

HCID 132461125,5-Dibromo-2-(propan-2-yl)pent-4-enoic acidYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a mixture of 7 g of water and 20 g of ethanol were dissolved 1.1 g of sodium hydroxide and 4.6 of the ethyl α-(3.3-dibromoallyl)isovalerate obtained above were added to the above solution. The mixture was stirred at room temperature overnight and, then, refluxed for 3 hours. The reaction mixture was then distilled to remove the ethanol and the residue was made acidic by the addition of dilute hydrochloric acid and extracted with diethyl ether. The ethereal layer was dried over anhydrous magnesium sulfate and the low-boiling fraction was distilled off. By the above procedure there were obtained 3.7 g of α-(3,3-dibromoallyl)isovaleric acid, the NMR spectrum of which is shown below [yield: 88% based on ethyl α-(3,3-dibromoallyl)isovalerate].

Workup

  1. customobtained
  2. additionabove were added to the above solution
  3. temperaturerefluxed for 3 hours
  4. distillationThe reaction mixture was then distilled
  5. customto remove the ethanol
  6. additionthe residue was made acidic by the addition of dilute hydrochloric acid
  7. extractionextracted with diethyl ether
  8. dry with materialThe ethereal layer was dried over anhydrous magnesium sulfate
  9. distillationthe low-boiling fraction was distilled off

Sources & evidence

ORD record
ord-1080eb6fdca14ba0be46f0f1156e4faf
Source dataset
uspto-grants-1983_10
Patent number
US04409238

Reaction notes

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