Synthesis of 3-methylanisole

Preparation of 3-methylanisole

Preparation of 3-methylanisole

Preparation of 3-methylanisole

The 1 mole of 3-cresol is treated rapidly with stirring, in a three-necked flask provided with a reflux condenser, stirrer, internal thermometer, and dropping funnel, with 1.25 mole of 10% sodium hydroxide. With vigorous stirring, 1 mole of dimethyl sulfate is added in such a way that the temperature remains below 40° C (water cooling). To complete the reaction and to destroy unchanged dimethyl sulfate, the mixture is then heated for 30 min on a boiling water bath. After cooling, the organic layer is separated off and the aqueous solution is extracted several times with ether. The combined organic phases are washed with dilute sodium carbonate and then with water, dried with calcium chloride, and fractionated. Unchanged 3-cresol can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 2-methylanisole is 80%, n20/D 1.513; b.p. 175-176 °C; b.p. 65°C/14mm; D=0.969 g/mL at 25 °C; 

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 206-207, (1973)

IUPAC Name

1-methoxy-3-methylbenzene

InChI

InChI=1S/C8H10O/c1-7-4-3-5-8(6-7)9-2/h3-6H,1-2H3

InChI Key

OSIGJGFTADMDOB-UHFFFAOYSA-N

Canonical SMILES

CC1=CC(=CC=C1)OC

Depositor-Supplied Synonyms

3-Methylanisole, 1-Methoxy-3-methylbenzene, 3-Methoxytoluene, 100-84-5, m-Methylanisole, m-Cresol methyl ether, M-METHOXYTOLUENE, Anisole, m-methyl-, Benzene, 1-methoxy-3-methyl-, Methyl m-cresyl ether, Methyl m-tolyl ether, 3-Methylmethoxybenzene, m-Cresyl methyl ether, Methyl 3-methylphenyl ether, 1-Methyl-3-methoxybenzene, 1-Methoxy-3-methyl-benzene, NSC 6255, UNII-UI9I3Y6WTZ, UI9I3Y6WTZ, CHEMBL349791, OSIGJGFTADMDOB-UHFFFAOYSA-N, EINECS 202-893-4, SBB061028, AI3-19476, 3-methoxy-1-methylbenzene, m-Methyl anisole, 3-methyl anisole, 3-methoxy toluene, AC1L1OYY, ACMC-1C3GF, 3-Methyl-1-methoxybenzene, METHYL-M-TOLYL ETHER, SCHEMBL12353, 149160_ALDRICH, Jsp000166, SCHEMBL12015250, CTK1A5099, NSC6255, MolPort-001-768-406, LABOTEST-BB LTBB003020, NSC-6255, STR09347, ZINC1693360, 7907AF, ANW-14378, BDBM50008537, ZINC01693360, AKOS000121157, AS01016, FR-1366, MCULE-7649681864, RP19469, RTR-000255, TRA0054603, AJ-30191, AK133073, CJ-06539, CJ-28311, KB-48840, LS-20215, OR034385, OR145939, DB-012728, TR-000255, FT-0628957, M0151, ST24038069, ST51047105, A800280, 3B4-1301, I01-5100, W-108936, InChI=1/C8H10O/c1-7-4-3-5-8(6-7)9-2/h3-6H,1-2H

Removed Synonyms

C8H10O, CID7530, 20369-34-0

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