Derivatives of 1,2,3,4-tetrahydroxybenzene. III. The synthesis of dill apiole and the extension of the Dakin reaction was written by Baker, Wilson;Jukes, E. H. T.;Subrahmanyam, C. A.. And the article was included in Journal of the Chemical Society in 1934.Formula: C7H6O3 This article mentions the following:
1,2,3,4-(HO)2C6H2(OMe)2 (I) is obtained in 5 g. yield by oxidizing 9.8 g. gallacetophenone 3,4-di-Me ether in 10% NaOH with 75 cc. 3% H2O2. I and allyl bromide in Me2CO-K2CO3 give an allyl ether, rearranged on heating to the 5-allyl derivative of I, b14 160-73° (impure), which reacted with CH2I2 in Me2CO-K2CO3 to give dill apiole (1,2-methylenedioxy-3,4-dimethoxy – 5 – allylbenzene), b16 172-3°. 1,2,3,4-Tetramethoxy-5-allylbenzene, b12 145°, m. 26°. 1,2,3-C6H3(OH)3, (CH2Br2 and K2CO3, refluxed for 30 hrs., give pyrogallol methylene ether, m. 65°. 7-Methoxy-8-acetyl-2-methylchromone, m. 161-2°, in quant. yield from the 7-HO derivative; this could not be hydrolyzed to the mono-Me ether or 2,4-diacetylresorcinol. 2,4-(HO)2C6H3COCH2Ph is oxidized by 3% H2O2 in N NaOH in an inert atm., giving 95% of PhCH2CO2H and 1,2,4-C6H3(OMe)3; 2,4-(HO)2C6H3COCH2C6H4OMe-p (ononetin) gives 60% of p-MeOC6H4CH2CO2H; homopiperonylresacetophenone gives 90% of β-piperonylpropionic acid; 2,4-HO(MeO)C6H3COCH2Ph gives 50% of PhCH2CO2H. Thus the Dakin reaction appears to be general. In the experiment, the researchers used many compounds, for example, Benzo[d][1,3]dioxol-4-ol (cas: 69393-72-2Formula: C7H6O3).
Benzo[d][1,3]dioxol-4-ol (cas: 69393-72-2) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Formula: C7H6O3
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts