Methanol → Ethyl 3-ethynylbenzoate

HRID 2080916Notes

Reaction equation

HRID 2080916 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7])#[CH:2].C[OH:13].N1[CH:19]=[CH:18]C=CC=1>ClCCl.CCCCCC>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([O:13][CH2:18][CH3:19])=[O:7])#[CH:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 1049PyridineHCID 200388133-Ethynylbenzoyl chloride

Product 1

HCID 15540684Ethyl 3-ethynylbenzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of m-ethynylbenzoic acid and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50° C. for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride. To the m-ethynylbenzoyl chloride obtained was added a solution having 298 μl (7.35 mmol) of methanol and 3.4 ml (42 mmol) of pyridine dissolved in 7 ml of dichloromethane under ice-cooling and then the resultant mixture was stirred at room temperature for one hour. After completion of the stirring, dichloromethane was removed by distillation under reduced pressure and 35 ml of water was added to the resultant residue and extracted with 35 ml of diethyl ether. The ether layer was dried over magnesium sulfate and the solvent was removed by distillation under reduced pressure using an evaporator. The resultant crude reaction product was dissolved in 15 ml of hexane at 70° C., insoluble matter was removed by filtration and the filtrate was cooled to obtain 0.74 g of ethyl 3-ethynylbenzoate which is a desired product as yellow solid. (Yield: 66E)

Workup

  1. additionwas added a solution
  2. temperaturecooling
  3. customAfter completion of the stirring, dichloromethane was removed by distillation under reduced pressure and 35 ml of water
  4. additionwas added to the resultant residue
  5. extractionextracted with 35 ml of diethyl ether
  6. dry with materialThe ether layer was dried over magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customan evaporator
  9. customThe resultant crude reaction product
  10. custominsoluble matter was removed by filtration
  11. temperaturethe filtrate was cooled

Sources & evidence

ORD record
ord-fd6baa8fe88c49c2b33b5a9bb0dc5525
Source dataset
uspto-grants-2011_04
Patent number
US07932398B2

Reaction notes

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