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

HRID 53438노트

반응식

HRID 53438 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-fab256f5282a417082c15991980bb1b0
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618969

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