Hydrochloric Acid → 2-[2-(4'-Chloro-biphenyl-4-YL)-2-oxo-ethyl]acrylic acid

HRID 1386842

반응식

HRID 1386842 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:12])[O:11][C:9](=[O:10])[CH2:8][C:6]1=[CH2:7].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.Cl>ClC1C=CC=CC=1Cl.O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:9](=[O:10])[CH2:8][C:6](=[CH2:7])[C:5]([OH:11])=[O:12])=[CH:22][CH:21]=2)=[CH:18][CH:19]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 163234-ChlorobiphenylHCID 75110Itaconic AnhydrideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 98393182-[2-(4'-Chloro-biphenyl-4-YL)-2-oxo-ethyl]acrylic acid수율 71.4%

시약·촉매·용매 2

HCID 962Water용매HCID 72391,2-Dichlorobenzene용매2회

반응 조건

온도
20 °C

실험 절차

212 g (1.59 mol) of anhydrous aluminum chloride are introduced into 1200 g of o-dichlorobenzene and brought to 45° C. with stirring. A solution of 78.5 g (0.7 mol) of itaconic anhydride and 132 g (0.7 mol) of 4-chlorobiphenyl in 600 g of o-dichlorobenzene at 45° C. is added dropwise in the course of one hour. The reaction mixture is stirred at 45° C. for one hour and then added to an ice-cold mixture of 1000 g of water and 142 g of hydrochloric acid (37%). The aqueous phase is separated off. The organic phase is washed three times with a mixture of 1000 g of water and 50 g of hydrochloric acid (37%) in each case. After washing three times, it is allowed to cool to approximately 20° C. and the colorless product is then filtered off with suction. This is then washed twice with 200 g of o-dichlorobenzene in each case. The product is dried at 40° C. and about 100 mbar until it is free of solvent and water. 150 g (0.50 mol) of 4-(4′-chlorobiphenyl-4-yl)-4-keto-2-methylenebutyric acid (71%) are obtained as a colorless, finely crystalline powder. Further product can be obtained by working up the mother liquor. The dichlorobenzene phase is washed a number of times with 0.1% strength by weight aqueous EDTA solution. After distilling off the dichlorobenzene in vacuo, further product is obtained by cooling the residue to 0° C., filtering off the colorless precipitate with suction and recrystallizing the residue, and the yield is increased to >85%. (HPLC purity 99.3-99.6%).

후처리

  1. custombrought to 45° C.
  2. stirringThe reaction mixture is stirred at 45° C. for one hour
  3. customThe aqueous phase is separated off
  4. washThe organic phase is washed three times
  5. additionwith a mixture of 1000 g of water and 50 g of hydrochloric acid (37%) in each case
  6. washAfter washing three times, it
  7. filtrationthe colorless product is then filtered off with suction
  8. washThis is then washed twice with 200 g of o-dichlorobenzene in each case
  9. customThe product is dried at 40° C.

출처 및 근거

ORD 기록
ord-0dafde85e6ae44fe99440e6e68ec5ac5
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265607B1

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