Acetic Acid → 4-(2,4-Dihydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-one

HRID 703622Notes

Reaction equation

C(O)(=O)C.[Si]([O:12][CH:13]1[CH2:18][C:17]([CH3:20])([CH3:19])[C:16]2([CH:22]=[CH:23][C:24](=[O:26])[CH3:25])[O:21][C:15]2([CH3:27])[CH2:14]1)(C(C)(C)C)(C)C>[Zn].C(Cl)(Cl)Cl>[OH:21][C:15]1([CH3:27])[CH2:14][CH:13]([OH:12])[CH2:18][C:17]([CH3:19])([CH3:20])[CH:16]1[CH:22]=[CH:23][C:24](=[O:26])[CH3:25]

Participants

Conditions

Temperature: 40 °C

Procedure

To 50 ml of a glacial acetic acid solution containing 600 mg of 4-[4-(t-butyldimethylsilyl)oxy-1,2-epoxy-2,6,6-trimethylcyclohexyl]but-3-en-2-one was added 8.9 g of a zinc powder at room temperature, and the mixture was vigorously stirred for 5 hours while maintaining the reaction temperature at about 40° C. To the reaction mixture was added 120 ml of chloroform, followed by stirring vigorously. Any insoluble matter was separated by filtration, and the filtrate was washed successively with water, a 5% aqueous solution of sodium hydrogen carbonate and water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent, etc. were removed by distillation under reduced pressure. Purification of the resiude by silica gel chromatography gave 241 mg (yield: 55%) of 4-(2,4-dihydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-one.

Workup

stirringby stirring vigorously
customAny insoluble matter was separated by filtration
washthe filtrate was washed successively with water
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent, etc. were removed by distillation under reduced pressure
customPurification of the resiude by silica gel chromatography

Sources & evidence

ORD record: ord-aa2c4fb4eb26436f8ac9321b9ff4fcde
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04983723

Reaction notes

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