Methyl Benzoate → Trimethyl orthoformate

HRID 2416179Notes

Reaction equation

HRID 2416179 reaction equation
[CH3:1][O:2][C:3](OC)([O:6][CH3:7])[O:4][CH3:5].[C:10]([O:18][CH3:19])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:20][N+](CCCC)(CCCC)CCCC>CO>[CH3:1][O:2][CH:3]([O:6][CH3:7])[O:4][CH3:5].[CH3:19][O:18][CH:10]([O:17][CH3:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7150Methyl BenzoateHCID 36209TributylmethylammoniumHCID 74613Tetramethyl orthocarbonate

Product 2

HCID 9005Trimethyl orthoformateHCID 62375Benzaldehyde dimethyl acetal

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1062 g of tetramethoxymethane, 303 g of methyl benzoate, 225 g of 60% methyltributylammonium methosulfate solution and 910 g of methanol were electrolyzed at 3 A. The voltage per gap was kept below 5 V, the temperature was 30° C., and the pumping rate was 190 l/h. After the electrolysis had ended, 10.0 GC area % of trimethoxymethane and 13.2 GC area % of benzaldehyde dimethyl acetal had formed in the electrolyte; tetramethoxyethane had been degraded from 42.5% to 25.6 GC area %, and methyl benzoate was down to 0.4 GC area %, having been converted to more than 95%. Low-boiling byproducts included methyl formate at 2.2 GC area % in the electrolyte.

Workup

  1. customwas 30° C.

Sources & evidence

ORD record
ord-ad31c5d3274e413788fc678a432849b9
Source dataset
uspto-grants-2004_11
Patent number
US06822124B2

Reaction notes

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