Synthesis of 4-methylanisole

Preparation of 4-methylanisole

Preparation of 4-methylanisole

Preparation of 4-methylanisole

The 1 mole of 4-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 4-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 1.511; b.p. 174 °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)





InChI Key


Canonical SMILES


MeSH Synonyms

4-methoxytoluene, 4-methyl anisole, 4-methylanisole, p-cresyl methyl ether, p-methyl anisole

Depositor-Supplied Synonyms

4-Methylanisole, 1-METHOXY-4-METHYLBENZENE, p-Methylanisole, 4-Methoxytoluene, 104-93-8, Benzene, 1-methoxy-4-methyl-, p-Methoxytoluene, Anisole, p-methyl-, p-Cresol methyl ether, Methyl p-tolyl ether, p-Tolyl methyl ether, Methyl p-cresyl ether, p-Cresyl methyl ether, 4-Methyl anisole, 1-Methyl-4-methoxybenzene, 4-Methyl-1-methoxybenzene, 4-Methylphenol methyl ether, Methyl 4-methylphenyl ether, 4-methylanisol, Methyl p-cresol, p-methyl anisole, Methyl p-methylphenyl ether, para-Methylanisole, Methyl-para-cresol, para-Methoxytoluene, 1-Methoxy-4-methyl-benzene, Toluene, 4-methoxy-, FEMA Number 2681, NSC 6254, para-Cresyl methyl ether, UNII-10FAI0OR9W, 10FAI0OR9W, FEMA No. 2681, CHEMBL154155, HSDB 5363, CHLICZRVGGXEOD-UHFFFAOYSA-N, EINECS 203-253-7, SBB060064, AI3-07621, p-methylanisol, p-Anisyl, p-Methoxy toluene, para-Methyl anisol, para-methyl anisole, 4-methylmethoxybenzene, 4-Methoxybenzylradical, AC1Q2QTD, ACMC-1BO1K, DSSTox_CID_6710, AC1L1PF9, DSSTox_RID_78191, DSSTox_GSID_26710, SCHEMBL12464, KSC483G0N, W268100_ALDRICH, WLN: 1OR D1, 148091_ALDRICH, SCHEMBL2489775, Jsp000478, SCHEMBL12015216, NSC6254, MolPort-001-783-105, NSC-6254, ZINC1693359, METHYL, (4-METHYLPHENOXY)-, Tox21_201081, 1091AA, ANW-15148, AR-1L1363, BDBM50008555, STL268886, ZINC01693359, AKOS000121016, LS-2901, MCULE-8571139509, RTR-033040, TRA0071269, NCGC00248917-01, NCGC00258634-01, AJ-30190, AK109358, AN-24698, CAS-104-93-8, CJ-28310, KB-39910, OR034327, OR146024, OR217889, OR227066, SC-79405, KB-242805, TR-033040, FT-0618970, M0149, ST24038073, ST51046311, EC 203-253-7, 3B4-1126, I01-5101, W-108799, InChI=1/C8H10O/c1-7-3-5-8(9-2)6-4-7/h3-6H,1-2H, 1071687-44-9, 3494-45-9

Removed Synonyms

C8H10O, CID7731, 105532-74-9

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