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

HRID 364628

반응식

HRID 364628 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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°.

후처리

  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)

출처 및 근거

ORD 기록
ord-0a8c8fb61d3b4bd8905b1173c1b7d879
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04605656

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