2,4,5-Trichlorophenol → 2,4,5-Trichlorophenyl 3-chloro-4-hydroxyphenylacetate

HRID 1859224노트

반응식

HRID 1859224 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([Cl:21])=[CH:16][C:15]=1O.C1CCC(N=C=NC2CCCCC2)CC1>C(OCC)(=O)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][C:15]2[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=2[Cl:13])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

참가 물질

6

반응물 3

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 1185343-Chloro-4-hydroxyphenylacetic acid

생성물 1

HCID 221234992,4,5-Trichlorophenyl 3-chloro-4-hydroxyphenylacetate수율 35.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4 g (21.6 mmol) of 3-chloro-4-hydroxyphenylacetic acid in 130 mL of ethyl acetate is slowly added to a solution of 4.7 g (23.6 mmol) of 2,4,5-trichlorophenol and 4.9 g (23.6 mmol) of DCC in 22 mL of dichloromethane and the reaction mixture is stirred overnight. The precipitate formed is separated by filtration and the solution is chilled to precipitate the rest of N,N-dicyclohexylurea. After a second filtration, the filtrate is washed three times with a solution of sodium bicarbonate, dried over MgSO4 and evaporated to dryness in a rotary evaporator. The resulting oil is chromatographed through silica gel eluting with hexanes and increasing amounts of dichloromethane. The desired product appears in the fraction eluted with 50% dichloromethane. After elimination of the solvent 2.8 g of product are isolated (34% yield), with the following analytical data: mp=77° C. Rf=0.33 (AcOEt/hexanes 3:7).

후처리

  1. customThe precipitate formed
  2. customis separated by filtration
  3. temperaturethe solution is chilled
  4. customto precipitate the rest of N,N-dicyclohexylurea
  5. filtrationAfter a second filtration
  6. washthe filtrate is washed three times with a solution of sodium bicarbonate
  7. dry with materialdried over MgSO4
  8. customevaporated to dryness in a rotary evaporator
  9. customThe resulting oil is chromatographed through silica gel eluting with hexanes
  10. temperatureincreasing amounts of dichloromethane
  11. washeluted with 50% dichloromethane

출처 및 근거

ORD 기록
ord-4597afb700fe4453916e2f88ef3666a0
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06153742

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