Phenol Ethers with a Pseudo Allylic Chain, -(Me)C:CH2 (III); Cresotinic Series; Synthesis of Thymol was written by Behal, A.;Tiffeneau, M.. And the article was included in Bulletin de la Societe Chimique de France in 1908.Synthetic Route of C10H12O3 This article mentions the following:
Me ether of pseudo-allylorthocresol (methyl-1-methoxy-2-pseudo-allylbenzene-3) MeC6H3(OMe)CMe:CH2. o-Cresotinic acid, tech., m. 163°, is esterified (1) (2) (3) with MeOH and H2SO4. Me ester m. 28°-30°, b. 235°. CH3MgI gives pseudoallyl-3-orthocresol, b. 220-225°, d20 = 1.040, nD20 = 1.543. This has the odor of thyme. Me sulfate gives pseudo-allyl-3-methyl-1-anisol-2, b. 217-18°, d0 = 0.9901, d15 = 0.9830, nD15 = 1.595. Reduction with Na and absolute alc. gives Me ether of isothymol, CH3C6H3.OCH3.CH(CH3)2, b. 210-3°, d0 = 0.9559, d19 = 0.9430, nD19 = 1.50725. An isothymol is obtained by demethylating with HI. Me ether of pseudoallylmetacresol (methyl-1-methoxy-3-pseudo-allylbenzene-4), MeC6H3(OMe)CMe:CH2. (1) (3) (4) Metacresotinic acid, m. 175-6°, is converted into its Me ester, b12 118-22°, d0 = 1.1629, d21 = 1.147, m. 27-8°. Methyl-methoxy-m-cresotinate, b. 259-61°, d0 = 1.1462, gives on saponification, methoxy-m-cresotinic acid, m. 103°. CH3MgI gives the alc., MeC6H3(OMe)CMe2OH, b11 129-30°, d0 = 1.0448, b. 240-6°. Dehydrated it gives methyl-1-methoxy-3-pseudo-allylbenzene-4, b. 216-9°, d0 = 0.9835. Methylthymol, MeC6H3(OMe).C3H7, is obtained by reducing with Na and absolute alc. (1) (3) (4) the pseudo-allyl-4-methyl-1-methoxy-4-benzene and oxidizing the product with KMnO4. Demethylation with HI yields thymol. In the experiment, the researchers used many compounds, for example, Methyl 2-methoxy-4-methylbenzoate (cas: 81245-24-1Synthetic Route of C10H12O3).
Methyl 2-methoxy-4-methylbenzoate (cas: 81245-24-1) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Synthetic Route of C10H12O3
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics