4,5-Dicyclopropyl-2-ethoxybenzenemethanol → 4,5-Dicyclopropyl-2-ethoxybenzaldehyde

HRID 531055Notes

Reaction equation

[CH:1]1([C:4]2[C:9]([CH:10]3[CH2:12][CH2:11]3)=[CH:8][C:7]([CH2:13][OH:14])=[C:6]([O:15][CH2:16][CH3:17])[CH:5]=2)[CH2:3][CH2:2]1>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH:1]1([C:4]2[C:9]([CH:10]3[CH2:12][CH2:11]3)=[CH:8][C:7]([CH:13]=[O:14])=[C:6]([O:15][CH2:16][CH3:17])[CH:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

Manganese dioxide (8.50 g) was added at room temperature to a toluene (50 mL) solution of (4,5-dicyclopropyl-2-ethoxyphenyl)methanol (2.84 g) in a nitrogen atmosphere, and the mixture was stirred at 80° C. for 1 hour. The reaction mixture was filtered through celite, and then, the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (2.68 g).

Workup

filtrationThe reaction mixture was filtered through celite
concentrationthe filtrate was concentrated
customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-77514b2c7a8641898ea80573a13b4059
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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