Methanol → Methyl 4-ethenylbenzoate

HRID 2120615Notes

Reaction equation

HRID 2120615 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[CH2:2].S(Cl)(Cl)=O.[CH3:16]O>C(Cl)Cl>[CH3:16][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 140984-Vinylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 583124Methyl 4-ethenylbenzoateYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Vinylbenzoic acid 69 (2.222 g, 15.00 mmol) was dissolved in 5 ml of methanol at room temperature. Thionyl chloride (1.094 ml, 15.00 mmol) was added dropwise and allowed to stir for 2 hours. The mixture was then heated to reflux for 20 minutes. Upon cooling the mixture was diluted with methylene chloride. The solvent was removed under a stream of nitrogen. The residue was purified by flash chromatography on silica eluted with 95:5 methylene chloride/methanol to give 2.370 g (97.4%) of methyl-4-vinylbenzoate 70 as a yellow oil.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 20 minutes
  3. temperatureUpon cooling the mixture
  4. customThe solvent was removed under a stream of nitrogen
  5. customThe residue was purified by flash chromatography on silica
  6. washeluted with 95:5 methylene chloride/methanol

Sources & evidence

ORD record
ord-eb92f88facdc4fa0bdb042fdfeb55515
Source dataset
uspto-grants-2004_02
Patent number
US06693098B2

Reaction notes

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