HCID 68644250, compound → HCID 86240729, compound

HRID 1158937Notes

Reaction equation

HRID 1158937 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([CH3:20])=[C:5]([O:10][CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[C:6]([CH3:9])=[N:7][CH:8]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[C:4]([CH3:20])=[C:5]([O:10][CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[C:6]([CH3:9])=[N:7][CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 68644250HCID 68644250, compound

Product 1

HCID 86240729HCID 86240729, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 4-(5-hydroxymethyl-2,4-dimethyl-pyridin-3-yloxymethyl)-benzonitrile (22) (5.6 g, 21 mmol) and manganese (IV) dioxide (9.1 g, 0.105 mol) in toluene (250 mL) was stirred at 60° C. for about 18 hours. Excess manganese (IV) dioxide was filtered through a celite pad and washed with ethyl acetate. The filtrate was evaporated to give 4-(5-formyl-2,4-dimethyl-pyridin-3-yloxymethyl)-benzonitrile (23) (3.6 g, 65% yield) as a colorless solid.

Workup

  1. filtrationExcess manganese (IV) dioxide was filtered through a celite pad
  2. washwashed with ethyl acetate
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d8d68c7bd1aa4b33bd331cd8a39ca732
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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