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

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]

Participants

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

temperatureThe reaction mixture is then maintained at 80° C. for 2 hours
temperaturethe mixture is cooled
extractionthe product is extracted with dichloromethane
washThe organic phases are washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated on a vacuum rotary evaporator
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

Linked notes

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