Water → Ethyl 3-(3,5-dichlorophenyl)prop-2-enoate

HRID 744109Notes

Reaction equation

HRID 744109 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[CH:21]=O.O>O1CCCC1>[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[CH:21]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 357463,5-Dichlorobenzaldehyde

Product 1

HCID 54039378Ethyl 3-(3,5-dichlorophenyl)prop-2-enoateYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a mixture of sodium hydride (0.84 g: 55% dispersion in mineral oil) and tetrahydrofuran (40 ml) was dropwise added a solution of ethyl diethylphosphonoacetate (4.33 g) in tetrahydrofuran (20 ml) with ice-cooling of 6° to 12° C. over a 12 minutes period. After stirring at room temperature for 30 minutes, to the mixture thus obtained was dropwise added a solution of 3,5-dichlorobenzaldehyde (3.07 g) in tetrahydrofuran (20 ml) with ice-cooling of 8° to 11° C. over a 10 minutes period. After stirring at room temperature for 4 hours, the reaction mixture was poured into water and extracted twice with ethyl acetate. The combined extract was washed with water, dried and concentrated. The residue was purified by flash column chromatography through silica gel (100 g). Fractions eluted with a 99:1 mixture of hexane and ethyl acetate were collected and worked up to afford the title compound (3.33 g), melting at 71°-73° C.

Workup

  1. temperaturecooling of 6° to 12° C. over a 12 minutes period
  2. customthus obtained
  3. temperaturecooling of 8° to 11° C. over a 10 minutes period
  4. stirringAfter stirring at room temperature for 4 hours
  5. extractionextracted twice with ethyl acetate
  6. extractionThe combined extract
  7. washwas washed with water
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified by flash column chromatography through silica gel (100 g)
  11. washFractions eluted with a 99:1 mixture of hexane and ethyl acetate
  12. customwere collected

Sources & evidence

ORD record
ord-cbd5faadc631483689fe93d850ed416e
Source dataset
uspto-grants-1996_09
Patent number
US05559109

Reaction notes

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