Hydrochloric Acid → 2-(Ethylthio)phenol

HRID 745692

반응식

HRID 745692 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:9]([S:11]SCC)[CH3:10].C(S)C>[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[CH2:9]([S:11][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[OH:7])[CH3:10]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 996Phenol2회HCID 6343EthanethiolHCID 8077Diethyl disulfide

생성물 1

HCID 1224072-(Ethylthio)phenol수율 41.3%

시약·촉매·용매 1

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-촉매

반응 조건

온도
156 °C

실험 절차

Zirconium tetrachloride (23.4 g, 0.1 mole) was added to phenol (141.2 g, 1.5 moles). The mixture was slowly heated to 156° C. under nitrogen and maintained at this temperature overnight while allowing HCl to escape. The mixture was cooled to ca. 100° C. and ethyl disulfide (122.3 g, 1 mole) was added. The mixture was heated under nitrogen while ethyl mercaptan was removed continuously by distillation. Heating was continued for a total of 7 hours during which temperature slowly increased to 198° C. Distillation of the mixture at 0.4 mm mercury to a maximum head temperature of 101° C. yielded 134.7 g of distillate. GC analysis indicated the distillate contained 53.4 g of phenol (38% recovered) and 63.7 g of ortho-(ethylthio)phenol (41% yield). Fractional distillation through a 5 inch Vigreux column yielded, after removal of phenol, a main fraction of 99.2% pure ortho-(ethylthio)phenol distilling at 125°-127° C. at 30 mm mercury.

후처리

  1. temperaturemaintained at this temperature overnight
  2. temperatureThe mixture was cooled to ca. 100° C.
  3. customwas removed continuously by distillation
  4. temperatureHeating
  5. customwas continued for a total of 7 hours during which temperature
  6. temperatureslowly increased to 198° C
  7. distillationDistillation of the mixture at 0.4 mm mercury to a maximum head temperature of 101° C.
  8. customyielded 134.7 g of distillate

출처 및 근거

ORD 기록
ord-5ecb19062b054583b038d6d2eaf790dc
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04599451

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