Water → 4-Fluorocinnamic acid

HRID 2352314Notes

Reaction equation

HRID 2352314 reaction equation
[OH-].[Na+].O.[F:4][C:5]1[CH:17]=[CH:16][C:8](/[CH:9]=[CH:10]/[C:11]([O:13]CC)=[O:12])=[CH:7][CH:6]=1>C(O)C>[F:4][C:5]1[CH:6]=[CH:7][C:8](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 5373059Ethyl 3-(4-fluorophenyl)acrylate

Product 1

HCID 15302344-Fluorocinnamic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4 g. of sodium hydroxide in 30 ml. of water is added to a solution of 19.4 g. (0.1 mole) of ethyl trans-4-fluorocinnamate (Compound LXV) in 350 ml. of ethanol, and the reaction mixture is stirred at 70° C. for 18 hours. The solvent is evaporated at reduced pressure, and the residue is dissolved in water. The solution is washed once with methyl t-butyl ether and acidified with 6N. hydrochloric acid. The resulting precipitate is washed twice with water and dried to obtain the product (15.5 g. (93%)). An analytical sample was recrystallized from ethyl acetate, m.p. 204°-206° C.

Workup

  1. customThe solvent is evaporated at reduced pressure
  2. dissolutionthe residue is dissolved in water
  3. washThe solution is washed once with methyl t-butyl ether
  4. washThe resulting precipitate is washed twice with water
  5. customdried
  6. customto obtain the product (15.5 g. (93%))
  7. customAn analytical sample was recrystallized from ethyl acetate, m.p. 204°-206° C.

Sources & evidence

ORD record
ord-712670e0560243c486513e22b793f197
Source dataset
uspto-grants-1989_10
Patent number
US04876280

Reaction notes

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