2,6-Dichlorobenzaldehyde → Ethyl 2,6-dichlorocinnamate

HRID 1506955Notes

Reaction equation

HRID 1506955 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[CH3:11][CH2:12][O:13][C:14]([CH2:16]P(OCC)(OCC)=O)=[O:15].CC([O-])(C)C.[K+]>C1COCC1>[CH2:12]([O:13][C:14](=[O:15])/[CH:16]=[CH:4]/[C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10])[CH3:11]

Participants

5

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 13345Triethyl phosphonoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 6010430Ethyl 2,6-dichlorocinnamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2,6-dichlorobenzaldehyde (5.0 g, 28.56 mmol) in THF was added triethyl phosphono acetate (6.4 g, 28.56 mmol) at 0° C. The reaction mixture was added t-BuOK (3.2 g, 28.56 mmol) at room temperature. The mixture was stirred for 10 h then the resulting mixture was quenched with 1N HCl, diluted with ether, washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by SiO2 gel column chromatography (4.3 g 40˜60%)

Workup

  1. customthe resulting mixture was quenched with 1N HCl
  2. additiondiluted with ether
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by SiO2 gel column chromatography (4.3 g 40˜60%)

Sources & evidence

ORD record
ord-fee917d8a52f453e93de55aa491f1915
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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