Sodium Hydroxide → HCID 53692823, compound

HRID 1732185Notes

Reaction equation

HRID 1732185 reaction equation
[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14](=[O:16])[CH3:15])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=O.[OH-].[Na+]>O.C(O)C>[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14](=[O:16])[CH:15]=[CH:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[F:17])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67970o-FluorobenzaldehydeHCID 123281882-(4-Acetyl-2,3-dichlorophenoxy)acetic acid

Product 1

HCID 53692823HCID 53692823, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To 500 ml of ethanol was added [2,3-dichloro-4-(1-oxo-ethyl)phenoxy]acetic acid (19.73 g, 0.075 mole), 2-fluorobenzaldehyde (13.63 g, 0.11 mole), sodium hydroxide (10 g, 0.25 mole) in 20 ml of water and 50 ml of ethanol with stirring under nitrogen. The reaction mixture was refluxed for a total of 11/2 hours. The reaction mixture was cooled, filtered, the gelatineous solid dispersed in water acidified with hydrochloric acid, stirred, filtered and washed with water. The residue was extracted with methylene chloride and ethyl acetate, washed with water, and concentrated under reduced pressure to give 15.2 g of [2,3-dichloro-4-(3-(2-fluorophenyl)-1-oxo-2-propenyl)phenoxy]acetic acid which melted at 191°-194° C. after purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. additionthe gelatineous solid dispersed in water
  4. stirringstirred
  5. filtrationfiltered
  6. washwashed with water
  7. extractionThe residue was extracted with methylene chloride and ethyl acetate
  8. washwashed with water
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-66587e3b6cfc4b8b87cb1c23cd2c49e5
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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