Benzoic acid, 2,4-dichloro-, ethyl ester → Ethanone, 1-(2,4-dichlorophenyl)-2-(3-pyridinyl)-

HRID 364628

反応式

HRID 364628 の反応式
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=O.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]C(OCC)=O)[CH:15]=1.C[O-].[Na+]>Cl>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[C:4](=[O:6])[CH2:20][C:16]1[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 42026Benzoic acid, 2,4-dichloro-, ethyl esterHCID 96490Ethyl 3-pyridylacetateHCID 10942334Sodium Methoxide

生成物 1

HCID 13488634Ethanone, 1-(2,4-dichlorophenyl)-2-(3-pyridinyl)-

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

A mixture of 27.6 g of ethyl 2,4-dichlorobenzoate and 20.81 g of ethyl 3-pyridylacetate at 20°-25° is treated portionwise with 10.59 g of sodium methoxide. The mixture is subsequently heated at 65°-70° and resulting readily volatile products are blown off with dry nitrogen. After 20 hours, the mixture is treated with 40 ml of concentrated hydrochloric acid and heated at reflux temperature for 18 hours. The mixture is washed with diethyl ether and the aqueous phase is made basic by adding concentrated ammonia and extracted with methylene chloride. The organic phase is concentrated and the crude product is chromatographed on silica gel with methylene chloride/methanol (98:2) to yield 2',4'-dichloro-2-(3-pyridyl)-acetophenone, which can be crystallized from diethyl ether/n-pentane and melts at 55°-56°.

後処理

  1. temperatureThe mixture is subsequently heated at 65°-70°
  2. customresulting readily volatile products
  3. temperatureheated
  4. temperatureat reflux temperature for 18 hours
  5. washThe mixture is washed with diethyl ether
  6. additionby adding concentrated ammonia
  7. extractionextracted with methylene chloride
  8. concentrationThe organic phase is concentrated
  9. customthe crude product is chromatographed on silica gel with methylene chloride/methanol (98:2)

出典と根拠

ORDレコード
ord-0a8c8fb61d3b4bd8905b1173c1b7d879
出典データセット
uspto-grants-1986_08
特許番号
US04605656

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