2-Chloroethanol → 5,7-Di-tert-butyl-3-[4-(2-hydroxyethoxy)phenyl]-benzofuran-2-one

HRID 22498

반응식

HRID 22498 반응식
Cl[CH2:2][CH2:3][OH:4].[C:5]([C:9]1[CH:10]=[C:11]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:12]2[O:16][C:15](=[O:17])[CH:14]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[C:13]=2[CH:25]=1)([CH3:8])([CH3:7])[CH3:6].Cl>[OH-].[Na+]>[C:5]([C:9]1[CH:10]=[C:11]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:12]2[O:16][C:15](=[O:17])[CH:14]([C:18]3[CH:19]=[CH:20][C:21]([O:24][CH2:2][CH2:3][OH:4])=[CH:22][CH:23]=3)[C:13]=2[CH:25]=1)([CH3:8])([CH3:7])[CH3:6]

참가 물질

5

반응물 3

HCID 342-ChloroethanolHCID 313Hydrochloric AcidHCID 189914135,7-Di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one

생성물 1

HCID 181835865,7-Di-tert-butyl-3-[4-(2-hydroxyethoxy)phenyl]-benzofuran-2-one수율 61.2%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
80 °C

실험 절차

1.0 ml (15.0 mmol) of 2-chloroethanol is added to a solution of 3.38 g (10.0 mmol) of 5,7-di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one in 30 ml of 1N sodium hydroxide solution heated to 80° C. The reaction mixture is then maintained at 80° C. for 2 hours, 50 ml of 1N hydrochloric acid are added, stirring is continued for 1 hour, the mixture is cooled, and the product is extracted with dichloromethane. The organic phases are washed with water, combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Crystallization of the residue from 8 ml of ethanol and 2 ml of water gives 2.34 g (61%) of 5,7-di-tert-butyl-3-[4-(2-hydroxyethoxy)phenyl]-benzofuran-2-one m.p. 132°-135° C. (compound (105), Table 1).

후처리

  1. temperatureThe reaction mixture is then maintained at 80° C. for 2 hours
  2. temperaturethe mixture is cooled
  3. extractionthe product is extracted with dichloromethane
  4. washThe organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated on a vacuum rotary evaporator
  7. customCrystallization of the residue from 8 ml of ethanol and 2 ml of water

출처 및 근거

ORD 기록
ord-4d7760fb1c6546e78dabc0c74bf1a512
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428162

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