Lignin. LII. The constitution of dehydrodiisoeugenol and its importance for the chemistry of lignin was written by Freudenberg, Karl;Richtzenhain, Hermann. And the article was included in Justus Liebigs Annalen der Chemie in 1942.SDS of cas: 1634-34-0 This article mentions the following:
The operations of methylation, the action of hot alkali and oxidation produce from lignin, Erdtman acid (I) and the amorphous dehydration product from coniferyl alc. (II) (by the action of FeCl3) veratric acid and a small amount of isohempinic acid, the formation of which results from the cleavage of a coumaran or chroman ring. The agreement of conclusive reactions of lignin and I (a coumaronecarboxylic acid) leads to the conclusion that, as in the case of the dehydration of isoeugenol, the dehydration of II gives, at least in part, a coumaran ring. The formula for dehydrodiisoeugenol (III) proposed by Erdtman is proved. The compound IV was cleaved with K in liquid NH3 (cf. C. A. 36, 5144.1) and methylated with Me2SO4 in 20% NaOH, giving a pale yellow oil, b0.01 145-50°; boiling with AcOHHBr for 4 h. in a N atm. gives 1-(3,4-dihydroxyphenyl)-2-(2,3-dihydroxy-5-propylphenyl)propane (V), m. 131°. V was synthesized as follows. 2-Hydroxy-3-methoxy-5-allylbenzaldehyde (Claisen and Eisleb, C. A. 8, 64) on catalytic reduction (Pd-BaSO4 in AcOH) gives 2-hydroxy-3-methoxy-5-propylbenzaldehyde, intense yellow oil, b10 155° (2,4-dinitrophenylhydrazone, red needles, m. 223°). Me2SO4 in 10% NaOH at 80° gives 2,3-dimethoxy-5-propylbenzaldehyde (VI), b10 155-6° (2,4-dinitrophenylhydrazone, red needles, m. 202°). VI (70 g.), 70 g. hippuric acid, 32 g. anhydrous AcONa and 120 cc. Ac2O, heated 2.5 h. on the water bath, give 72 g. of the azlactone, fiery yellow, m. 158-9°; boiling with 350 cc. 10% NaOH for 5 h. gives 2,3-dimethoxy-5-propylphenylpyruvic acid, m. 130-1°, which is isolated through the NaHSO3 compound; 100 cc. 6% H2O2 and the acid in about 600 cc. NaHCO3 at -5° give 39.5 g. (83% of the azlactone) of 2,3-dimethoxy-5-propylphenylacetic acid (VII), m. 93-4°. The acid chloride from 10 g. VII (using 32 cc. SOCl2 for 2.5 h. at 60°) and 16 g. of veratrole in 40 cc. CS2 with 11.2 g. AlCl3, warmed 2 h. at 60°, give 6.35 g. of 2,3-dimethoxy-5-propylbenzyl 3,4-dimethoxyphenyl ketone, m. 87-8°; warming of the crude ketone with 1.2 g. Na in 20 cc. absolute MeOH, removal of the MeOH, addition of 15 cc. C6H6 and 10 cc. MeI and heating of the mixture on the water bath for 5 h. gives 1-keto-1-(3,4-dimethoxyphenyl)-2-(2,3-dimethoxy-5-propylphenyl)propane, m. 101°; Clemmensen reduction and demethylation give V; the yield is poor. In the experiment, the researchers used many compounds, for example, 2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0SDS of cas: 1634-34-0).
2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.SDS of cas: 1634-34-0
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts