Thionyl Chloride → Methyl 2-(4'-chloromethylphenyl)benzoate

HRID 53438Notes

Reaction equation

HRID 53438 reaction equation
O[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.S(Cl)([Cl:21])=O>N1C=CC=CC=1.C(Cl)Cl>[Cl:21][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

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 15380881Methyl 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carboxylate

Product 1

HCID 15380884Methyl 2-(4'-chloromethylphenyl)benzoateYield 88%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

2.0 g (8.25 mmol) of methyl 2-(4'-hydroxymethylphenyl)benzoate was dissolved in 1.31 g of pyridine and methylene chloride (20 ml). 1.47 g (12.4 mmol) of thionyl chloride was dropwise added thereto at room temperature, followed by stirring as such for 16 hours and under reflux by heating for 5 hours. After the reaction liquid was cooled and concentrated, a saturated aqueous solution of sodium hydrogencarbonate was added thereto, followed by the extraction with methylene chloride. The organic phase was washed with water, dried and subjected to vacuum concentration. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 1.89 g of the title compound as an oil (yield 88%).

Workup

  1. customat room temperature
  2. temperatureunder reflux
  3. temperatureby heating for 5 hours
  4. customAfter the reaction liquid
  5. temperaturewas cooled
  6. concentrationconcentrated
  7. additiona saturated aqueous solution of sodium hydrogencarbonate was added
  8. extractionfollowed by the extraction with methylene chloride
  9. washThe organic phase was washed with water
  10. customdried
  11. concentrationsubjected to vacuum concentration
  12. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-fab256f5282a417082c15991980bb1b0
Source dataset
uspto-grants-1997_04
Patent number
US05618969

Reaction notes

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