Benzene → HCID 18981480, compound

HRID 1441151Notes

Reaction equation

HRID 1441151 reaction equation
[CH3:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[C:14](O)(=[O:17])[C:15]#[CH:16].C1C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:14]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][C:5]1[CH:12]=[CH:13][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:17])[C:15]#[CH:16]

Participants

6

Reactant 3

HCID 241BenzeneHCID 10110Propiolic AcidHCID 12293196Poly(oxy-1,4-butanediyl), α-(4-methylphenyl)-ω-hydroxy-

Product 1

HCID 18981480HCID 18981480, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

A mixture of 1 g of 4-(4-methylphenoxy)butanol, 1.1 g of propiolic acid, 0.005 g of p-toluenesulfonic acid and 25 ml of benzene was refluxed with stirring for six hours while water formed was removed by a Dean-Stark water separator. After the reaction was completed, the reaction solution was washed successively with a 5% aqueous sodium bicarbonate solution and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the obtained residue was subjected to silicagel column chromatography to yield 1.15 g of 4-(4-methylphenoxy)butyl propiolate (compound 11).

Workup

  1. temperaturewas refluxed
  2. customformed
  3. customwas removed by a Dean-Stark water separator
  4. washthe reaction solution was washed successively with a 5% aqueous sodium bicarbonate solution
  5. dry with materiala saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-86e9022db0b54e41b5e7aa8933cb18e7
Source dataset
uspto-grants-1996_03
Patent number
US05502242

Reaction notes

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