Sodium Carbonate → 4-Ethynylbenzaldehyde

HRID 1007736Notes

Reaction equation

HRID 1007736 reaction equation
C[Si](C)(C)[C:3]1[CH:10]=[CH:9][C:6](C=O)=[C:5]([C:11]#[CH:12])[CH:4]=1.[C:15](=[O:18])([O-])[O-].[Na+].[Na+]>CO>[C:11]([C:5]1[CH:6]=[CH:9][C:10]([CH:15]=[O:18])=[CH:3][CH:4]=1)#[CH:12]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 22665199HCID 22665199, compound

Product 1

HCID 27716454-EthynylbenzaldehydeYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The trimethylsilyl groups were subsequently subjected to a deprotecting reaction in accordance with reaction (2) in FIG. 2. Specifically, 4.0 g of 4-trimethylsilyl ethynyl benzaldehyde was dissolved in 20 mL of methanol, the solution was stirred for 30 minutes under nitrogen gas, 0.19 g of sodium carbonate was added, and the product was stirred for another 3 hours at room temperature. The solvent was removed at a reduced pressure, the residue was washed with a 5% aqueous solution of sodium bicarbonate and extracted with dichloromethane, anhydrous sodium sulfate was added, and the product was dried. The dried product was filtered off and the solvent was removed at a reduced pressure. The product was dried in a vacuum, yielding the target compound 4-ethynyl benzaldehyde with an aldehyde odor as white crystals with the yield of 99%.

Workup

  1. stirringthe product was stirred for another 3 hours at room temperature
  2. customThe solvent was removed at a reduced pressure
  3. washthe residue was washed with a 5% aqueous solution of sodium bicarbonate
  4. extractionextracted with dichloromethane, anhydrous sodium sulfate
  5. additionwas added
  6. customthe product was dried
  7. filtrationThe dried product was filtered off
  8. customthe solvent was removed at a reduced pressure
  9. customThe product was dried in a vacuum

Sources & evidence

ORD record
ord-d0d87b825b2b4c2c9c50702218c9c18b
Source dataset
uspto-grants-2004_09
Patent number
US06797390B2

Reaction notes

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