4-Toluenesulfonyl chloride → Methyl 2-(4'-p-toluenesulfonyloxymethylphenyl)benzoate

HRID 742799Notes

Reaction equation

HRID 742799 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1.[H-].[Na+].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.[Cl-].[NH4+]>O1CCCC1>[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([O:1][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 15380881Methyl 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carboxylate

Product 1

HCID 15380883Methyl 2-(4'-p-toluenesulfonyloxymethylphenyl)benzoateYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.0 g (41 mmol) of methyl 2-(4'-hydroxymethylphenyl)benzoate was dissolved in tetrahydrofuran (200 ml). 2.0 g (50 mmol) of a 60% sodium hydride was added thereto under cooling with ice, followed by stirring for one hour. A solution of 8.65 g (45.4 mmol) of p-toluenesulfonyl chloride in tetrahydrofuran (50 ml) was dropwise added thereto. Then, the reaction was effected at room temperature for 2 hours and further reflux by heating was effected for 4 hours. The reaction liquid was cooled and added to a saturated aqueous solution of ammonium chloride. The resulting mixture was extracted with chloroform (200 ml). After the organic phase was washed with water and dried, it was subjected to vacuum concentration. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 13.4 g of the title compound as a wax (yield 82%).

Workup

  1. temperatureunder cooling with ice
  2. waitThen, the reaction was effected at room temperature for 2 hours
  3. temperaturefurther reflux
  4. temperatureby heating
  5. waitwas effected for 4 hours
  6. customThe reaction liquid
  7. temperaturewas cooled
  8. extractionThe resulting mixture was extracted with chloroform (200 ml)
  9. washAfter the organic phase was washed with water
  10. customdried
  11. concentrationit was subjected to vacuum concentration
  12. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-11fbdf63e6474d96a14bbf31e1cb46e5
Source dataset
uspto-grants-1996_09
Patent number
US05554757

Reaction notes

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