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

HRID 2272477Notes

Reaction equation

HRID 2272477 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

4

Reactant 1

HCID 90423712(4,5-Dicyclopropyl-2-isopropoxyphenyl)methanol

Product 1

HCID 904237454,5-Dicyclopropyl-2-isopropoxybenzaldehydeYield 94.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

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

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

Sources & evidence

ORD record
ord-e4b7a1a518b34bbaa100eb30b7a53087
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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