2,4,6-Trimethoxybenzaldehyde

Syringaldehyde is easily methylated or ethylated with the known procedures in high yields forming the highly-desirable 3,4,5-trimethoxybenzaldehyde or the 3,5-di-MeO-4-EtO-benzaldehyde (Escaline, 72, 40-60 mg, 8-12 hrs.). 

Increased single bond character in a carbonyl group is associated with a decreased carbon—oxygen stretching frequency Among the three compounds benzaldehyde 2 4 6 trimethoxybenzaldehyde and 2 4 6 trinitrobenzaldehyde which one will have the lowest frequency carbonyl absorption" Which one will have the highest" ... 

Catechol Derivatives. An elegant synthesis of trimethoxybenzaldehyde [86-81-7] (4) starting from quaiacol [90-05-1] (5) and formaldehyde (75) has been developed. The reaction sequence is as follows ... 

Deacylation has been studied with 2,4,6-trimethoxybenzaldehyde so that the increased aromatic reactivity would permit behaviour in weaker acid media to be examined654. First-order rate coefficients obtained at 80 °C are given in Table 224. Whilst the rate coefficients are identical in each acid up to 2 M, there-... 

A group of arylalkylketones containing a basic substituent in the side chain shows CNS activities. Roletamide (190) is a hypnotic agent. It is prepared from 3,4,5-trimethoxybenzaldehyde (187) by addition of sodium acetylide (to give 188), followed by Jones oxidation of ethynylarylketone 189. Michael addition... 

The synthesis of the furan-imidazole derivatives, shown in Scheme 2, were also described by Wang et al. [34]. Reaction of 4-(dimethylamino)benzalde-hyde (20) with trimethylsilylcyanide (TMS)-CN in the presence of Znl2 produced the TMS cyanohydrin 21. Compound 21 was treated with LDA followed by the addition of 3,4,5-trimethoxybenzaldehyde to give the benzoin intermediate 22. Oxidation with CUSO4 in aqueous pyridine, followed by reaction with 3-furaldehyde in acetic acid, produced the substituted imidazole 23. 

Synthesis of the amino-triazole derivative (43) was performed in the authors laboratory by Pati et al. [52] (Scheme 7). Substituted benzyl bromide was reacted with triphenylphosphine to produce the phosphonium bromide starting material, 44. The Wittig reagent, obtained by treatment with sodium hydride, was reacted with 3,4,5-trimethoxybenzaldehyde 18 to generate the nitro-stilbene 45 in good yields. The alkyne 46 was obtained by bromination of the stilbene, followed by didehydrobromination. Compound 46 was then reacted under thermal conditions with benzyl azides... 

A frequently reported spectrophotometric technique for the determination of hydralazine is based on reactions with aromatic aldehydes to form hydrazones with absorption in the visible region. Luk yanchikova et al (5 +) used p-nitrobenzaldehyde Wesley-Hadzija and Abaffy (55) and Ruggieri (56) used p-dimethylaminobenzaldehyde Luk yanchi-kova (57,58) used cinnamaldehyde Schulert (33) used p-hydroxybenzaldehyde and Zak et al (59) used p-methoxy-benzaldehyde, after testing cinnamaldehyde, salicylaldehyde, 3, +,5-trimethoxybenzaldehyde, and 1-naphthaldehyde. 

Orders for certain chemicals used to make psychedelics (especially large orders in suspect areas) are sometimes checked by narcs. Indole, lithium aluminum hydride, trimethoxybenzaldehyde, phenyl-2-propanol, diethylamine, olivetol and ergotamine are among those watched. The vast majority of the homologs and analogs described here are, however, legal to manufacture and use. 

Mix 5.5 g 3,4,5-trimethoxybenzaldehyde (or analog), 2.5 g NH4 Acetate, 25 ml nitroethane (or equimolar amount nitromethane for the analog), 25 ml benzene and reflux about twenty hours water being removed with a Dean-Stark tube. Cool and wash with 2X25 ml water, 2X25 ml saturated NaHS03 and 2X25 ml water and dry and evaporate in vacuum the benzene to get (I). Reduce the nitropropene (or nitrostyrene) by any method such as follows To a stirred suspension of 3 g lithium aluminum hydride in 50 ml tetrahydrofuran, add 4.4 g (I) in 50 ml tetrahydrofuran and reflux one hour. Cool in ice bath and treat slowly with wet tetrahydrofuran... 

All of the other syntheses begin with 3,4,5-trimethoxybenzaldehyde. According to one of them, condensation of 3,4,5-trimethoxybenzaldehyde with 3-ethoxy- or 3-anilinopropionitrile... 

Trimethoprim has also been synthesized by condensing 3,4,5-trimethoxybenzaldehyde with malonic acid dinitrile in a Knoevenagel reaction, which forms the derivative (33.1.53), which is partially reduced to the enamine (33.1.54) by hydrogen using a palladium on carbon catalyst, which upon being reacted with guanidine is transformed into trimethoprim [52,53]. 

Trimethoxybenzaldehyde has been prepared by the classical Rosenmund3-5 reduction, from 5-hydroxyvanillin by methylation,6 and by oxidation of 3,4,5-trimethoxybenzyl alcohol.7... 

The reaction has been carried out on large- and small-scale batches (Note 10). This modification,8 as exemplified by 3,4,5-trimethoxybenzaldehyde, has been applied by the submitters to the preparation of other aldehydes9 such as 3,4-dimethyl-benzaldehyde10 (90% yield), 3-benzyloxy-4,5-dimethoxybenz-aldehyde11 (88% yield, with retention of the benzyl group), and 3-methoxy-4-nitrobenzaldehyde12 (62% yield, with retention of the nitro group). 

The conjugate addition of aryl dithiane anions to 2-butenolide has been examined as a route to ( )-podorhizol and ( )-isopodophyllotoxone (78JOC985). The dithiane of piperonal (802) was deprotonated and reacted with 2-butenolide to give the lactone anion which was trapped in turn with 3,4,5-trimethoxybenzaldehyde to afford a mixture of the threo and erythro aldol products (803). Desulfurization of the erythro dithiane with Raney nickel gave ( )-podorhizol (804 Scheme 188). 

---