Iodine → 2,4-Dichloro-3-ethyl-6-nitrophenol

HRID 1086021

반응식

HRID 1086021 반응식
II.C(C1C=CC(S(O)(=O)=[O:12])=CC=1)C.ClCl.Cl[C:18]1[C:23]([Cl:24])=[C:22]([CH2:25][CH3:26])[C:21]([Cl:27])=[CH:20][C:19]=1S(O)(=O)=O.[N+:32]([O-])([OH:34])=[O:33]>S(=O)(=O)(O)O.O>[Cl:24][C:23]1[C:22]([CH2:25][CH3:26])=[C:21]([Cl:27])[CH:20]=[C:19]([N+:32]([O-:34])=[O:33])[C:18]=1[OH:12]

참가 물질

8

반응물 5

HCID 807IodineHCID 944Nitric AcidHCID 74024-Ethylbenzenesulfonic acidHCID 24526ChlorineHCID 145974402,3,5-Trichloro-4-ethylbenzenesulfonic acid

생성물 1

HCID 70203392,4-Dichloro-3-ethyl-6-nitrophenol

시약·촉매·용매 2

HCID 962Water용매4회HCID 1118Sulfuric Acid용매3회

실험 절차

Iodine (5 parts) was dissolved in 96% sulfuric acid (1000 parts) and 4-ethylbenzenesulfonic acid (186 parts) was added thereto. Chlorine (about 235 parts) was introduced therein, while being stirred at a temperature of 40° to 60° C. Then, a 2,3,5-trichloro-4-ethylbenzenesulfonic acid content in the reaction mixture reached 78.3%. Successively, water (200 parts) was added to the reaction mixture so as to make a ratio of sulfuric acid to water 8:2, and the reaction mixture was subjected to steam distillation at a temperature of 160° to 200° C., thereby performing desulfonation reaction. Mixed acid consisting of 67% nitric acid (110 parts) and concentrated sulfuric acid (174 parts) was added dropwise to the desulfonation reaction product isolated from water, while being stirred at a temperature of 20° to 40° C., and the mixture was kept at that temperature for 1 to 3 hours. Thereafter, the reaction mixture was poured into water (950 parts) at a temperature of 30° C. or below. The reaction product was separated from water and then washed with water. The crude product of 2,3,5-trichloro-4-ethylnitrobenzene (220 parts) was added to a mixture of methanol (1560 parts), water (200 parts) and potassium hydroxide (240 parts), and the resulting mixture was refluxed for 4 hours. Thereafter, the reaction mixture was cooled to ambient temperature to deposit precipitate. The precipitate separated and washed with methanol and then water was placed in 20 % sulfuric acid (510 parts). The mixture was stirred for 3 hours at a temperature of 70° to 75° C., and then cooled to produce crystals of 2,4-dichloro-3-ethyl-6-nitrophenol. The crystals were collected on a filter, washed with water and then dried to obtain a desired product (141.8 parts). The over-all yield from 4-ethylbenzenesulfonic acid was found to be 60.1 %. The product had a melting point of 45.1° to 46.5° C.

후처리

  1. distillationthe reaction mixture was subjected to steam distillation at a temperature of 160° to 200° C.
  2. customperforming desulfonation reaction
  3. additionMixed acid
  4. additionwas added dropwise to the desulfonation reaction product
  5. stirringwhile being stirred at a temperature of 20° to 40° C.
  6. customThe reaction product was separated from water
  7. washwashed with water
  8. additionThe crude product of 2,3,5-trichloro-4-ethylnitrobenzene (220 parts) was added to a mixture of methanol (1560 parts), water (200 parts) and potassium hydroxide (240 parts)
  9. temperaturethe resulting mixture was refluxed for 4 hours
  10. customThe precipitate separated
  11. washwashed with methanol
  12. stirringThe mixture was stirred for 3 hours at a temperature of 70° to 75° C.
  13. temperaturecooled

출처 및 근거

ORD 기록
ord-ba506011cf844737b47558b264dcf79e
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05012015

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