2,6-Dichlorobenzaldehyde → ethyl 2,6-dichlorocinnamate

HRID 1348785Notes

Reaction equation

HRID 1348785 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.C[C:12]([CH3:15])([O-:14])C.[K+].[Cl-].[NH4+].C1C[O:22][CH2:21][CH2:20]1>>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=[CH:20][C:21]([O:14][CH2:12][CH3:15])=[O:22]

Participants

5

Reactant 4

HCID 67372,6-DichlorobenzaldehydeHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 4102414ethyl 2,6-dichlorocinnamateYield 65.1%

Procedure

To a solution of 2,6-dichlorobenzaldehyde (350 mg, 2.0 mmol) and triethyl phosphonoacetate (448 mg, 2.6 mmol) in THF (5 mL), potassium tert-butoxide (291 mg, 2.6 mmol) was added under ice cooling, and at the same temperature, the mixture was stirred for 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. Further, the residue was purified by column chromatography on silica gel (hexane/ethyl acetate=50/1) to yield the title compound as a colorless syrupy substance (yield: 65.1%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customFurther, the residue was purified by column chromatography on silica gel (hexane/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-8bb409b930ce4a54a2446cd87a4a4f61
Source dataset
uspto-grants-2007_05
Patent number
US07211577B2

Reaction notes

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