Benzaldehyde → HCID 53981476, compound

HRID 1732183Notes

Reaction equation

HRID 1732183 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].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14](=[O:16])[CH:15]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 123281882-(4-Acetyl-2,3-dichlorophenoxy)acetic acid

Product 1

HCID 53981476HCID 53981476, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a stirred suspension of [2,3-dichloro-4-(1-oxo-ethyl)phenoxy]acetic acid (15.78 g 0.06 mole) in 75 ml ethanol was added benzaldehyde (7.95 g, 0.075 mole) with stirring under nitrogen, followed by NaOH (8.0 g, 0.20 mole) in 16 ml of water. An additional 150 ml of ethanol was added and stirring was continued. The reaction mixture was heated at reflux for 11/2 hours, poured into ice water and acidified with hydrochloric acid. The mixture was extracted with ethyl acetate and methylene chloride, washed with dilute hydrochloric acid, then brine, dried over magnesium sulfate and concentrated under reduced pressure to give 8.7 g of [2,3-dichloro-4-(1-oxo-3-phenyl-2-propenyl)phenoxy]acetic acid which melted at 190°-191° C. after recrystallization from acetonitrile.

Workup

  1. stirringstirring
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 11/2 hours
  4. extractionThe mixture was extracted with ethyl acetate and methylene chloride
  5. washwashed with dilute hydrochloric acid
  6. dry with materialbrine, dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53ab9208569c40ebbfd84e130ca02edc
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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