Methanol → (E)-Methyl 3-(3,4-difluorophenyl)acrylate

HRID 1383781Notes

Reaction equation

HRID 1383781 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[F:13])/[CH:5]=[CH:6]/[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH3:19]O>>[CH3:19][O:8][C:7](=[O:9])/[CH:6]=[CH:5]/[C:4]1[CH:10]=[CH:11][C:12]([F:13])=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2733300trans-3,4-Difluorocinnamic acid

Product 1

HCID 20668596(E)-Methyl 3-(3,4-difluorophenyl)acrylateYield 100%

Procedure

To a solution of trans-3,4-difluorocinnamic acid (10 g, 54 mmol) in 300 mL methanol was added concentrated sulfuric acid (2 mL). The solution was stirred 48 h at ambient temperature and then concentrated in vacuo. The residue was taken up in ethyl acetate (500 mL) and washed with saturated sodium bicarbonate (2×100 mL), brine (1×100 mL), dried with magnesium sulfate, and concentrated in vacuo to provide trans-3,4-difluorocinnamic acid methyl ester (10.7 g, 54 mmol, 100%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with saturated sodium bicarbonate (2×100 mL), brine (1×100 mL)
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59506ce5ba7c4d2a97feeca284884598
Source dataset
uspto-grants-2001_07
Patent number
US06255315B1

Reaction notes

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