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

HRID 982817Notes

Reaction equation

HRID 982817 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 chromatography on a silica gel column (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 chromatography on a silica gel column (hexane/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-2b0cdd5ef3e64d30b4c0e5e1c5605237
Source dataset
uspto-grants-2005_03
Patent number
US06861428B2

Reaction notes

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