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

HRID 1386843

反応式

HRID 1386843 の反応式
[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>O.ClC1C=CC=CC=1Cl>[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

参加物

7

反応物 4

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

生成物 1

HCID 98393182-[2-(4'-Chloro-biphenyl-4-YL)-2-oxo-ethyl]acrylic acid収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 72391,2-Dichlorobenzene溶媒

反応条件

温度
20 °C

実験手順

212 g (1.59 mol) of anhydrous aluminum chloride are introduced into 1800 g of o-dichlorobenzene and the mixture is brought to 45° C. with stirring. A solid mixture of 78.5 g (0.7 mol) of itaconic anhydride and 132 g (0.7 mol) of 4-chlorobiphenyl is added in the course of one hour. The reaction mixture is stirred at 45° C. for two hours and then added to an ice-cold mixture of 900 g of water and 100 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 25 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 150 g of ethanol/water 90:10 in each case. The product is dried at 80° C. and about 110 mbar until free of solvent and water. 148 g (0.49 mol) of 4-(4′-chlorobiphenyl-4-yl)-4-keto-2-methylenebutyric acid (70%) are obtained as a colorless, finely crystalline powder. By working up the mother liquor, as described in Example 1, the yield is increased to 87%. (HPLC purity 99.3-99.5%).

後処理

  1. customis brought to 45° C.
  2. additionis added in the course of one hour
  3. stirringThe reaction mixture is stirred at 45° C. for two hours
  4. customThe aqueous phase is separated off
  5. washThe organic phase is washed three times
  6. additionwith a mixture of 1000 g of water and 25 g of hydrochloric acid (37%) in each case
  7. washAfter washing three times, it
  8. filtrationthe colorless product is then filtered off with suction
  9. washThis is then washed twice with 150 g of ethanol/water 90:10 in each case
  10. customThe product is dried at 80° C.

出典と根拠

ORDレコード
ord-e2ebcfaafbfb45389f80d8c376d5f235
出典データセット
uspto-grants-2001_07
特許番号
US06265607B1

関連ノート

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