Hydrogen Peroxide → (2-Methylquinolin-4-yl)methanol

HRID 1477382Notes

Reaction equation

HRID 1477382 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.S(=O)(=O)(O)O.OO.[OH-:19].[NH4+].[CH3:21]O>O.[Fe]>[CH3:1][C:2]1[CH:11]=[C:10]([CH2:21][OH:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 1118Sulfuric AcidHCID 70602-MethylquinolineHCID 14923Ammonium Hydroxide

Product 1

HCID 10149033(2-Methylquinolin-4-yl)methanol

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

To a mixture of 2-methylquinoline (43.0 g, 0.3 mol), iron (5.04 g, 0.09 mol), FeSO4.7H2O (25.0 g, 0.09 mol) in methanol (400 mL) and water (200 mL) was added sulfuric acid (conc., 16.0 mL, 0.3 mol) at 0° C., and then H2O2 (160 mL) was slowly added at 0° C. The mixture was then warmed to room temperature and stirred overnight. The solution was diluted with water, basified with ammonium hydroxide, and extracted with ethyl acetate. The combined extract was washed with brine, dried and concentrated. Recrystallization from ethyl ether/hexane to give (2-Methylquinolin-4-yl)methanol (12.0 g). ESI (M+H)+173.9.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe combined extract
  3. washwas washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customRecrystallization from ethyl ether/hexane

Sources & evidence

ORD record
ord-cbf17598a437473dbc76ee9c68809f20
Source dataset
uspto-grants-2016_08
Patent number
US09403775B2

Reaction notes

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