1-Methylnaphthalene → 1-Naphthaldehyde

HRID 1979658Notes

Reaction equation

HRID 1979658 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C([O:16]P(OCCCC)(OCCCC)=O)CCC>OS(O)(=O)=O>[C:2]1([CH:1]=[O:16])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70021-MethylnaphthaleneHCID 31357Tributyl Phosphate

Product 1

HCID 61951-NaphthaldehydeYield 25.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The same reaction was tried in a modified cell, without the crank 23. 2 g (14 mmol) of 1-methylnaphthalene in 3 g of tributylphosphate was allowed to react for 40 hours with electrochemically produced Co(III) sulphate at 40°-45° C. The electrolyte solution was composed of 0.12M Co(II) sulphate in 2M H2SO4. The current was 200 mA. The organic material isolated from this run was placed on a silica gel column, which was eluted with a solution of 5% ether in petroleum ether (bp=60°-80° C.). The initial band consisted of 860 mg (6 mmol, 43%) of starting material. The second band yielded 447 mg (2.9 mmol) of 1-naphthaldehyde. The aldehyde yield was 36% based on consumed starting material. The aldehyde yield was 36% based on consumed starting material. The infrared spectrum of the product was identical to that of an authentic sample.

Workup

  1. customThe same reaction
  2. customThe organic material isolated from this run
  3. washwas eluted with a solution of 5% ether in petroleum ether (bp=60°-80° C.)

Sources & evidence

ORD record
ord-a134b7b10f5347c1a934a6c3b6241602
Source dataset
uspto-grants-1984_11
Patent number
US04482438

Reaction notes

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