Methanol → Methyl 4-ethynylbenzoate

HRID 1826064Notes

Reaction equation

HRID 1826064 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[CH:2].[CH3:12][OH:13]>O1CCCC1>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:13][CH3:12])=[O:8])=[CH:5][CH:4]=1)#[CH:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 109317874-ethynylbenzoyl Chloride

Product 1

HCID 640163Methyl 4-ethynylbenzoateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then, a solution prepared by dissolving 24.7 g (0.15 mole) of 4-ethynylbenzoic acid chloride in 30 ml of tetrahydrofuran was added dropwise into 300 ml of methanol cooled in an ice bath. After the addition was completed, the reaction solution became turbid in 20 minutes. The reaction mixture was kept being stirred for 2 hours in the ice bath and then stirred at the room temperature for further 2 hours. The reaction mixture was filtered and dried and 21 g (the yield: 87%) of methyl 4-ethynylbenzoate was obtained.

Workup

  1. customThen, a solution prepared
  2. temperaturecooled in an ice bath
  3. additionAfter the addition
  4. customin 20 minutes
  5. filtrationThe reaction mixture was filtered
  6. customdried

Sources & evidence

ORD record
ord-9a28317085ce421fb7579d2e9feec8c3
Source dataset
uspto-grants-2006_05
Patent number
US07049371B2

Reaction notes

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