Ethanol → Ethyl (2E)-3-(2,4-dichlorophenyl)prop-2-enoate

HRID 12603Notes

Reaction equation

HRID 12603 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12].OS(O)(=O)=O.[CH2:19](O)[CH3:20]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([O:13][CH2:19][CH3:20])=[O:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 688026TRANS-2,4-DICHLOROCINNAMIC ACID

Product 1

HCID 5706328Ethyl (2E)-3-(2,4-dichlorophenyl)prop-2-enoate

Procedure

To a stirred solution of (2E)-3-(2,4-Dichlorophenyl)acrylic acid (10 g, 46 mmol) in ethanol (60 ml) was added conc. H2SO4 (2.5 ml). The mixture was heated to reflux and for 48 H, then allowed to cool, concentrated in vacuo, dissolved in ethyl acetate, washed three times with 4N NaOH, dried over sodium sulfate and concentrated in vacuo to afford ethyl (2E)-3-(2,4-dichlorophenyl)acrylate (10.7 g) as pale brown crystals. 1H NMR δ (ppm)(CDCl3): 8.00 (1 H, d, J=16.1 Hz), 7.55 (1 H, d, J=8.5 Hz), 7.44 (1 H, d, J=1.9 Hz), 7.26 (1 H, dd, J=2.0, 8.4 Hz), 6.41 (1 H, d, J=16.1 Hz), 4.28 (2 H, q, J=7.1 Hz), 1.34 (3 H, t, J=7.1 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux and for 48 H
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. dissolutiondissolved in ethyl acetate
  6. washwashed three times with 4N NaOH
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a2d937961c84f83bb3d0b101579b0e6
Source dataset
uspto-grants-2010_06
Patent number
US07728022B2

Reaction notes

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