(8-Methylnaphthalen-1-yl)methanol → 8-Methyl-1-naphthaldehyde

HRID 729782Notes

Reaction equation

HRID 729782 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][OH:13])=[CH:9][CH:8]=[CH:7]2>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH:12]=[O:13])=[CH:9][CH:8]=[CH:7]2

Participants

3

Reactant 1

HCID 15618201(8-Methylnaphthalen-1-yl)methanol

Product 1

HCID 155634878-Methyl-1-naphthaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1-L 4-neck equipped with an overhead stirrer, a condenser and a thermocouple was charged with 8-methyl-1-napthalenemethanol (18.5 g, 0.107 mol) in CH2Cl2 (500 mL) and stirred at room temperature under N2. Solid Mn(IV)O2 (61 g, 0.7 mol) was carefully added and the reaction was stirred at room temperature for 3 h, then at 40° C. for 6 h and then at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (500 mL), filtered and the filtrate was washed with 1N HCl and then dried over MgSO4. The resulting crude material was purified using silica gel chromatography (8/2 hexane/ethyl acetate) to yield 8-methyl-naphthalene-1-carbaldehyde as a solid.

Workup

  1. stirringthe reaction was stirred at room temperature for 3 h
  2. customat room temperature
  3. customovernight
  4. filtrationfiltered
  5. washthe filtrate was washed with 1N HCl
  6. dry with materialdried over MgSO4
  7. customThe resulting crude material was purified

Sources & evidence

ORD record
ord-09c073ae4fe041d9bf7833299ec62aeb
Source dataset
uspto-grants-2009_09
Patent number
US07582649B2

Reaction notes

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