4-Methoxyphenol → HCID 19983618, compound

HRID 1460279Notes

Reaction equation

HRID 1460279 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H][H].Cl[CH2:15][CH2:16][CH2:17][C:18]#[CH:19]>CS(C)=O.O>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:19][CH2:18][CH2:17][C:16]#[CH:15])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 90154-MethoxyphenolHCID 24758Sodium hydrideHCID 843081-Pentyne, 5-chloro-HCID 178418361HCID 178418361, compound

Product 1

HCID 19983618HCID 19983618, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a suspension of 960 mg (40 mmol) of sodium hydride in 25 mL of dimethyl sulfoxide is added 4.97 g (40 mmol) of 4-methoxyphenol. After the evolution of hydrogen has ceased, 4.10 g (40 mmol, 4.24 mL) of 5-chloro-1-pentyne is added. The mixture is maintained with stirring for 16.5 hours, is diluted with water and is extracted with ethyl ether. The ethereal extract is dried over magnesium sulfate, filtered and rotoevaporated to give 7.1 g (93%) of title compound.

Workup

  1. temperatureThe mixture is maintained
  2. extractionis extracted with ethyl ether
  3. extractionThe ethereal extract
  4. dry with materialis dried over magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ccd762879bd04ef48572fa922e5561e1
Source dataset
uspto-grants-1991_12
Patent number
US05070207

Reaction notes

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