Sulfuric Acid → 4-Methoxybenzaldehyde

HRID 2057680Notes

Reaction equation

HRID 2057680 reaction equation
[Pb]=[O:2].S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1>O>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]=[O:2])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1118Sulfuric Acid2×HCID 77314-MethylanisoleHCID 14827Lead monoxideHCID 24436Sodium Sulfate

Product 1

HCID 312444-MethoxybenzaldehydeYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In this example a divided electrochemical cell provided with a lead oxide anode and cathode and an anion exchange membrane sold under the tradename IONAC 3475 was used. The anolyte was prepared by admixing 25 grams of sulfuric acid with 250 grams of water and thereafter adding 100 grams of manganous sulfate. The catholyte was prepared by adding 25 grams of sulfuric acid to 250 grams of water and thereafter adding 30 grams of sodium sulfate. The anolyte solution and catholyte solution were added to the respective reservoirs and thereafter 50 grams of p-methoxytoluene was slowly added to the anolyte solution. The electrical energy which was used consisted of an E applied voltage ranging from 4.0 to 6.0 volts along with about 2.0 amps while maintaining the current density at a rate of about 80 milliamps/cm2. In addition, the reaction was run at ambient temperature and atmospheric pressure. The solution was passed through the cell and condenser and back to the cell by use of a pump. The reaction was run for a period of 3.33 hours at the end of which time a gas liquid chromatographic analysis disclosed a yield of 46% anisaldehyde with a selectivity to the aldehyde of greater than 50%, current efficiencies of 85-100% being observed.

Workup

  1. customThe anolyte was prepared
  2. customThe catholyte was prepared
  3. additionThe anolyte solution and catholyte solution were added to the respective reservoirs
  4. temperaturewhile maintaining the current density at a rate of about 80 milliamps/cm2
  5. customwas run at ambient temperature

Sources & evidence

ORD record
ord-ed3ff5fa1fd346019245661679d6e849
Source dataset
uspto-grants-1980_07
Patent number
US04212711

Reaction notes

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