The transformation of the commercially available 2,3.4-trimethoxybenzaldehyde to 2,3,4,5-tetramethoxytoluene using a Dakin reaction to insert the extra oxygen, formylation, reduction and methylation of the phenolic hydroxyl group is described.

2-Acetyl-1-hydroxynaphthalene was converted into the title compound in three steps (bromination, substitution and methylation). 1-Methoxynaphthalene on bromination, substitution and acetylation, respectively, also yielded the target compound.

Phenol ethers Q 0270An Alternative Route for the Synthesis of 2,3,4,5-Tetramethoxytoluene. -Commercially available 2,3,4-trimethoxybenzaldehyde is transformed to 2,3,4,5-tetramethoxytoluene using a Dakin reaction to insert the extra oxygen, formylation, reduction, and methylation of the phenolic hydroxyl group. -(VERA, W. J.; CHINEA, K.; BANERJEE*, A. K.; J. Chem. Res. 2009, 3, 186-187; Cent. Quim., Inst. Venez. Invest. Cient., Caracas 1020-A, Venez.; Eng.) -H. Toeppel 34-070

The transformation of 6-methoxy-1-tetralone 3 into the title acid 9 has been accomplished. The overall yield of the acid is superior to that reported.

2-Acetyl-1-hydroxynaphthalene was converted into 1,4-dimethoxy-2-naphthoxyacetic acid in seven steps (methylation, Bayer-Villiger oxidation, hydrolysis, bromination, methylation, alkylation and hydrolysis). 2-Hydroxy-1,4-naphthoquinone on acetylation, aromatization, methylation and hydrolysis, respectively, also yielded the title compound.