Potassium Hydroxide → 2-Benzylacrylic Acid

HRID 375838Notes

Reaction equation

HRID 375838 reaction equation
[CH2:1]=[C:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O-:5])=[O:4].[OH-].[K+]>CO>[CH2:1]=[C:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21909952HCID 21909952, compound

Product 1

HCID 3035712-Benzylacrylic AcidYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ethyl (α-methylenebenzenepropanoate of Step 8 (4.6 g, 24.3 mmol) was dissolved in methanol (12 mL) and then reacted with 2N potassium hydroxide (24 mL) solution. The mixture was stirred at room temperature for 4 hours and concentrated by evaporation. The residue was diluted with water and washed with ether. The aqueous layer was acidified to pH 2 with 1N HCl and then extracted with ethyl acetate. The extracts were dried (MgSO4) and evaporated to give the title compound as colorless oil (2.8 g, 66% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure.

Workup

  1. concentrationconcentrated by evaporation
  2. additionThe residue was diluted with water
  3. washwashed with ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extracts were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-19bd23d9a198495b9d94c92f842f59c1
Source dataset
uspto-grants-1996_01
Patent number
US05488066

Reaction notes

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