Potassium Hydroxide → α-Ethenylbenzenepropanoic acid

HRID 580032Notes

Reaction equation

HRID 580032 reaction equation
Cl.N[OH:3].[OH-].[K+].[CH2:6]([CH:13]([CH:17]=[CH2:18])[C:14](Cl)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CO.C1COCC1>[CH2:6]([CH:13]([CH:17]=[CH2:18])[C:14]([OH:3])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 11287032HCID 11287032, compound

Product 1

HCID 10976022α-Ethenylbenzenepropanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of hydroxylamine hydrochloride (0.455 g, 6.55 mmole) in 25 ml of absolute methyl alcohol and a solution of potassium hydroxide (0.85 g, 12.8 mmole) in 25 ml of absolute methyl alcohol were cooled to 0° C. and mixed together. A solution of 2-benzylbut-3-eneoic acid chloride, prepared as described in A above, in 10 ml of dry THF was added at 0° C. to the mixed solutions with stirring. The cooling bath was removed and the mixture was stirred at room temperature for 20 minutes. The pH of the mixture was adjusted to 4.0 with 5% hydrochloric acid and the mixture was evaporated to remove methyl alcohol. The aqueous concentrate was saturated with sodium chloride and extracted four times with 75 ml portions of ethyl acetate. The extracts were combined, washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness. The 2-benzylbut-3-eneoic acid N-hydroxamide obtained as a pale brownish yellow oil was used without further purification in the following step.

Workup

  1. additionmixed together
  2. additionwas added at 0° C. to the mixed solutions
  3. customThe cooling bath was removed
  4. stirringthe mixture was stirred at room temperature for 20 minutes
  5. customthe mixture was evaporated
  6. customto remove methyl alcohol
  7. concentrationThe aqueous concentrate
  8. extractionextracted four times with 75 ml portions of ethyl acetate
  9. washwashed with brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-6470881aa95f45e7afa8f3248dfede3e
Source dataset
uspto-grants-1988_06
Patent number
US04751296

Reaction notes

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