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

HRID 1664610Notes

Reaction equation

HRID 1664610 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-c6f3d28437ad44d9a000fe73f800340f
Source dataset
uspto-grants-2011_10
Patent number
US08039471B2

Reaction notes

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