2-Methyl-5-phenyladamantan-2-ol → 1-(2-Phenylhexahydro-2,5-methanopentalen-3a-yl)ethanone

HRID 2405743Notes

Reaction equation

[CH3:1][C:2]1([OH:18])[CH:9]2[CH2:10][CH:5]3[CH2:6][C:7]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.Cl[O-].[Na+]>C1COCC1.C(O)(=O)C.O>[C:12]1([C:7]23[CH2:6][CH:5]4[CH2:4][C:3]([C:2](=[O:18])[CH3:1])([CH2:11]2)[CH:9]([CH2:10]4)[CH2:8]3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-methyl-5-phenyladamantan-2-ol (300 g) in THF (710 ml) and acetic acid (160 ml) was added at 0° C. to a solution (8.3%, 3330 ml) of sodium hypochloride in water. After addition of n-tetrabutylammonium iodide (25.6 g), the mixture was heated to 25° C. within 90 minutes. After full conversion and phase separation, the organic phase was washed repeatedly with water. After full concentration of the organic phase, the residue was taken up in methanol (525 ml). Potassium hydroxide (82 g) was added and the mixture was stirred at room temperature. After adding tert-butyl methyl ether, the mixture was washed repeatedly with water. The organic solution was clarified with activated carbon and concentrated fully under reduced pressure. This gave 1-(2-phenylhexahydro-2,5-methanopentalen-3a-yl)ethanone (320 g) as an oil.

Workup

customAfter full conversion and phase separation
washthe organic phase was washed repeatedly with water
concentrationAfter full concentration of the organic phase
additionPotassium hydroxide (82 g) was added
additionAfter adding tert-butyl methyl ether
washthe mixture was washed repeatedly with water
concentrationconcentrated fully under reduced pressure

Sources & evidence

ORD record: ord-28e50e8b8c3b4731b73cbbe2ac800b44
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809325B2

Reaction notes

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