Hydrochloric Acid → cis-Cinnamic acid

HRID 2376679Notes

Reaction equation

HRID 2376679 reaction equation
[C:1]1(/[CH:7]=[CH:8]\[C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].Cl>O1CCCC1.O>[C:1]1(/[CH:7]=[CH:8]\[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6428458Methyl cinnamate, (Z)-

Product 1

HCID 5372954cis-Cinnamic acidYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1.1 g of methyl (Z)-3-phenylacrylate are dissolved in a mixture of 30 ml of tetrahydrofuran and 10 ml of water, and 340 mg of lithium hydroxide are added. The mixture is stirred at 60° C. After four hours, the reaction mixture is acidified by adding one molar hydrochloric acid solution and extracted five times with 50 ml of ethyl acetate each time. The combined organic phases are dried over MgSO4 and then the solvent is removed in vacuo. 900 mg of (Z)-3-phenylacrylic acid are obtained as an oil.

Workup

  1. additionare added
  2. extractionextracted five times with 50 ml of ethyl acetate each time
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-26e519e4e5314010adc0081b654de16b
Source dataset
uspto-grants-2008_12
Patent number
US07468369B2

Reaction notes

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