Potassium Hydroxide → alpha-Methyl-3-fluorocinnamic acid

HRID 1606707Notes

Reaction equation

HRID 1606707 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([O:14]C(=O)CC)(=[O:13])[CH2:11][CH3:12].C([O-])(=O)CC.[Na+].[OH-].[K+]>>[CH3:12][C:11](=[CH:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=1)[C:10]([OH:14])=[O:13]

Participants

5

Reactant 4

HCID 14797Potassium HydroxideHCID 31263Propionic anhydrideHCID 680093-FluorobenzaldehydeHCID 2723816Sodium Propionate

Product 1

HCID 53421834alpha-Methyl-3-fluorocinnamic acidYield 71.5%

Procedure

A mixture of 49.6 g. (0.4 mole) of meta-fluorobenzaldehyde, 66 ml. (0.51 mole) of propionic anhydride and 38.4 g. (0.4 mole) of sodium propionate were heated at 135°C for 19 hours. The reaction was cooled and to it was added a liter of 1 normal potassium hydroxide and the mixture was extracted with ether. The aqueous phase was freed of residual ether and acidified to pH 2 with hydrochloric acid. The product which crystallized was filtered and dried to give 51.5 grams of α-methyl-3-fluorocinnamic acid, melting point 95°-97°C.

Workup

  1. additionA mixture of 49.6 g
  2. temperatureThe reaction was cooled and to it
  3. extractionthe mixture was extracted with ether
  4. customThe product which crystallized
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-1b0ade5fb02e4ef1aef224e39a40fbf4
Source dataset
uspto-grants-1976_04
Patent number
US03953520

Reaction notes

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