(4,5-Dicyclopropyl-2-isopropoxyphenyl)methanol → 4,5-Dicyclopropyl-2-isopropoxybenzaldehyde

HRID 531029Notes

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][CH:16]([CH3:18])[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][CH:16]([CH3:18])[CH3:17])[CH:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

Manganese dioxide (14.7 g) was added at room temperature to a toluene (80 mL) solution of (4,5-dicyclopropyl-2-isopropoxyphenyl)methanol (5.22 g), and the mixture was stirred at 80° C. for 1 hour in a nitrogen atmosphere. 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 (4.88 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-c7b722ac0f184841bef005833c5135a5
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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