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

HRID 22498
Notes
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Reaction equation

HRID 22498 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4d7760fb1c6546e78dabc0c74bf1a512
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05428162

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes