O-Cresol → 1-Methyl-2-(prop-2-yn-1-yloxy)benzene

HRID 429034Notes

Reaction equation

HRID 429034 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Cl)[C:8]#[CH:9].[C:11]1([CH3:18])[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[CH3:18][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=1[O:17][CH2:9][C:8]#[CH:7]

Participants

5

Reactant 3

HCID 335O-CresolHCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyne

Product 1

HCID 123605171-Methyl-2-(prop-2-yn-1-yloxy)benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

245 g of potassium carbonate and 75 ml of propargyl chloride are added to a solutions of 96 g of o-cresol in 1500 ml of acetonitrile. The mixture is now heated for 14 hours at 65°, cooled to room temperature, and filtered with suction, and the filtrate is evaporated. The residue is taken up in 150 ml of ethyl acetate, the mixture is filtered with suction and the filtrate is evaporated. This gives 134 g of the total compound as a pale brown oil.

Workup

  1. temperatureThe mixture is now heated for 14 hours at 65°
  2. filtrationfiltered with suction
  3. customthe filtrate is evaporated
  4. filtrationthe mixture is filtered with suction
  5. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-e4419a08497b44ed82657aaff3c684ae
Source dataset
uspto-grants-2001_11
Patent number
US06316389B1

Reaction notes

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