Behavior of lignin models on nitration was written by Chuksanova, A. A.;Sergeeva, L. L.;Shorygina, N. N.. And the article was included in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya in 1959.Product Details of 3929-47-3 This article mentions the following:
Nitration of simple analogs of lignin was studied. If the phenolic group was protected, the reaction occurred in the 6-position, while condensation of the alc. took place as well. If the model compound had an open phenolic group in p-position relative to the side-chain, the latter was apt to be cleaved. The results indicated the multiplicity of possible reactions in the course of nitration of lignin. Reduction of Et 3-(4-hydroxy-3-methoxyphenyl)propionate with LiAlH4 gave 1-(4-hydroxy-3-methoxyphenyl)-3-propanol, m. 65°. This treated with fuming HNO3 in CCl4 at 5° 0.5 hr. gave a brown amorphous lignin-like product, containing 5.3% N. Reduction of Et 3-(3,4-dimethoxyphenyl)propionate with LiAlH4 gave 3-(3,4-dimethoxyphenyl)propanol, b1 171°, nitrated as above to about 50% 3-(6-nitro-3,4-dimethoxyphenyl)-1-propanol, m. 92-3°. Condensation of vanillin with EtNO2 and reduction of the product gave 1-(4-hydroxy-3-methoxyphenyl)-2-propanone, b4 155°, which with LiAlH4 gave the corresponding 2-propanol, m. 52°, which nitrated to a bright orange C10H13O5N, m. 95-6°. Condensation of veratraldehyde with EtNO2 and reduction of the product gave 1-(3,4-dimethoxyphenyl)-2-propanone (I), b1 148°, which with LiAlH4 gave the corresponding 2-propanol, m. 44°, nitrated to 3-(6-nitro-3,4-dimethoxyphenyl)-2-propanol, m. 99-100°; with larger amounts of HNO3 the product was 1-(6-nitro-3,4-dimethoxyphenyl)-2-propanone, m. 125.5°, also formed on nitration of I; semicarbazone m. 206°. Vanillin with EtMgBr gave 1-(4-hydroxy-3-methoxyphenyl)-1-propanol, m. 85-6°, nitrated to 3,5-dinitroguaiacol, m. 122°, while a larger amount of HNO3 gave a dimeric product, C20H24O9N2, m. 140-1°. Veratraldehyde with EtMgBr gave 1-(3,4-dimethoxyphenyl)-1-propanol, b2 146°, nitrated to 1-(6-nitro-3,4-dimethoxyphenyl)-1-propanol, m. 86°, a trace of, evidently, 1-(2,6-dinitro-3,4-dimethoxyphenyl)-1-propanol, m. 95°, and two products, C22H28O9N2, one of which m. 206° (oxidation with 15% HNO3 gave 4,5-dinitroveratrole), the other m. 134°, also oxidized to 4,5-dinitroveratrole with hot HNO3. Nitration as above of com. sulfate process lignin and hydrolytic lignin gave products with 3.75-4.27% total N and 0.48-0.66% nitrate N. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Product Details of 3929-47-3).
3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Product Details of 3929-47-3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem