Water → 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone

HRID 651360Notes

Reaction equation

[C:1]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=[C:7]([CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C(I)C=CC=1)=[O:20].O>C(#N)C.O>[CH3:16][C:7]1([OH:20])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10](=[O:11])[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5.0 g of 2,6-di-t-butyl-p-cresol in 90 ml of acetonitrile/water (5/1) was added 10.5 g of bistrifluoroacetoxyiodobenzene with stirring at 0° C. After stirring for 30 minutes, 90 ml of water was added and the reaction solution was extracted three times with 50 ml of dichloromethane and washed four times with 60 ml of water. Organic layers were dried over anhydrous sodium sulfate, then concentrated under reduced pressure and the precipitating crystal was filtered to give a crude crystal, which was recrystallized from hexane to give 4-methyl-4-hydroxy-2,6-di-t-butylcyclohexa-2,5-diene-1-one as a pale yellow solid. The yield was 3.0 g (55%).

Workup

stirringAfter stirring for 30 minutes
extractionthe reaction solution was extracted three times with 50 ml of dichloromethane
washwashed four times with 60 ml of water
dry with materialOrganic layers were dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
filtrationthe precipitating crystal was filtered
customto give a crude crystal, which
customwas recrystallized from hexane

Sources & evidence

ORD record: ord-ec6e649ed0ab460da14e321f0da99a51
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06280893B1

Reaction notes

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