Acetic Acid → 3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid

HRID 1980210

반응식

HRID 1980210 반응식
[Cl:1][C:2]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:6]=C(C)[CH:8]=[CH:9][CH:10]=1.Br.O=O.OO.[C:25]([OH:28])(=[O:27])[CH3:26]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:15]=[C:14]([C:16]([F:17])([F:19])[F:18])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:6]=[C:26]([CH:8]=[CH:9][CH:10]=1)[C:25]([OH:28])=[O:27]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 784Hydrogen PeroxideHCID 977OxygenHCID 3084880Benzene, 2-Chloro-1-(3-methylphenoxy)-4-(trifluoromethyl)-

생성물 1

HCID 916853-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid수율 85.1%

시약·촉매·용매 1

HCID 61372Cobalt(II) acetate tetrahydrate촉매

반응 조건

온도
90 °C

실험 절차

Into a three liter flask is added 1.3 liters of acetic acid, 614 g. (1.90 mole) of 88.8% pure 3-(2-chloro-4-trifluoromethylphenoxy)toluene, and 32.0 g. (0.128 mole) of cobalt acetate tetrahydrate. To this stirred pink solution is added 20.0 ml (0.173 mole) of 47% aqueous hydrogen bromide whereupon the solution turns blue. The solution is then heated to 90° C. and a flow of oxygen (100%, 2.19×10-2 mole/min) is initiated. Hydrogen peroxide 10.0 ml (30%, 0.088 mole) is then added via a syringe to the solution and the exotherm raises the reaction temperature to 98° C. within 5 minutes. The reaction is monitored by thin layer chromatography and is complete within 4 hours. Isolation of the oxidation product 3-(2-chloro-4-trifluoromethylphenoxy)benzoic acid from the reaction mixture is accomplished by distillation of the acetic acid solvent, neutralization with aqueous sodium hydroxide to a pH of 11, filtration to remove the insoluble cobalt hydroxides and acidification of the filtrate with sulfuric acid to precipitate the product, which is filtered and dried to give 680.3 g of 85.1% 3-(2-chloro-4-trifluoromethylphenoxy)benzoic acid. This represents of 96.1% yield of this product based on the 3-(2-chloro-4-trifluoromethylphenoxy)toluene starting material.

후처리

  1. temperaturethe exotherm raises the reaction temperature to 98° C. within 5 minutes
  2. distillationIsolation of the oxidation product 3-(2-chloro-4-trifluoromethylphenoxy)benzoic acid from the reaction mixture is accomplished by distillation of the acetic acid solvent, neutralization with aqueous sodium hydroxide to a pH of 11, filtration
  3. customto remove the insoluble cobalt hydroxides and acidification of the filtrate with sulfuric acid
  4. customto precipitate the product, which
  5. filtrationis filtered
  6. customdried

출처 및 근거

ORD 기록
ord-2af6859fa02c4b80976beb5646aa6fe5
출처 데이터셋
uspto-grants-1984_11
특허 번호
US04485254

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