Potassium Hydroxide → 2-Benzylacrylic Acid

HRID 2186313Notes

Reaction equation

HRID 2186313 reaction equation
[CH2:1]=[C:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5]CC)=[O:4].[OH-].[K+]>CO>[CH2:1]=[C:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11084648Ethyl 2-benzylacrylate

Product 1

HCID 3035712-Benzylacrylic AcidYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ethyl α-methylenebenzenepropanoate of Step 7 (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 (Na2SO4) 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 (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-d26314651cad4fd38676b2b528a059c2
Source dataset
uspto-grants-2002_06
Patent number
US06403648B2

Reaction notes

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