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

HRID 742802ノート

反応式

HRID 742802 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-2bb1a01e7e994a8bbf81d6be5762a26d
出典データセット
uspto-grants-1996_09
特許番号
US05554757

反応ノート

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