Hydrochloric Acid → 2-(4-Fluorophenoxy)-5-nitro-α-oxobenzenepropanoic acid

HRID 866600노트

반응식

HRID 866600 반응식
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=2[CH:9]=O)=[CH:4][CH:3]=1.[C:20](=[O:23])(O)[O-:21].[K+].[C:25](NCC(O)=O)(=[O:27])C.C(OC(=O)C)(=O)C.Cl>O.C(O)(=O)C>[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=2[CH2:9][C:25](=[O:27])[C:20]([OH:21])=[O:23])=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 10972AcetylglycineHCID 516893Potassium BicarbonateHCID 22767921HCID 22767921, 화합물

생성물 1

HCID 214270062-(4-Fluorophenoxy)-5-nitro-α-oxobenzenepropanoic acid

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

실험 절차

183.4 G. of 2-(4-fluoro-phenoxy)-5-nitro-benzaldehyde are stirred at reflux for 20 minutes together with 71 g. of potassium bicarbonate and 82 g. of acetylglycine in 395 ml. of acetic anhydride. Then, there are added successively 1.62 liters of glacial acetic acid, 870 ml. of water and 675 ml. of concentrated hydrochloric acid, and the mixture is stirred for 5 hours at reflux. The resulting mixture is cooled and 1.2 liters of water are added. The mixture is extracted with 3.1 liters of methylene chloride in 3 portions. The methylene chloride solutions are washed twice with 2 liters of water each time and subsequently extracted with a solution of 250 g. of sodium carbonate in 4.5 liters of water. The obtained bicarbonate solutions are acidified with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solutions are dried over sodium sulfate and evaporated in vacuo. The crystalline residue is boiled out with 400 ml. of benzene. The crystals are removed by filtration and there is obtained 2-(4-fluoro-phenoxy)-5-nitro-phenylpyruvic acid having a melting point of 142°-143° C. By concentration of the filtrate, there is obtained an additional amount of this compound.

후처리

  1. temperatureat reflux for 20 minutes together with 71 g
  2. temperatureat reflux
  3. temperatureThe resulting mixture is cooled
  4. extractionThe mixture is extracted with 3.1 liters of methylene chloride in 3 portions
  5. washThe methylene chloride solutions are washed twice with 2 liters of water each time
  6. extractionsubsequently extracted with a solution of 250 g
  7. extractionextracted with ethyl acetate
  8. dry with materialThe ethyl acetate solutions are dried over sodium sulfate
  9. customevaporated in vacuo
  10. customThe crystals are removed by filtration

출처 및 근거

ORD 기록
ord-859163acbb0a45d88998403efa08c90b
출처 데이터셋
uspto-grants-1978_07
특허 번호
US04100173

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