Synthesis of anisole

Preparation of anisole

Alternative Names:  Methoxybenzene; Methyl phenyl ether; Benzene, methoxy-; Anisol;

Preparation of anisole

Preparation of anisole

30 g phenol are dissolved in 100 ml water, and 40 ml concentrated solution of sodium hydroxide in a round-bottomed flask of 500 ml capacity. 50 ml dimethyl sulfate are added to the solution, which is then continually shaken. The beginning of the reaction is shown by the solution’s becoming turbid, like milk, while a light layer of oil floating on the aqueous solution takes the place of the heavy dimethyl sulfate at the bottom of the liquid. A fair amount of heat is evolved in the action, and care is taken by cooling that the temperature (to be examined by means of a thermometer dipping in the liquid) remains at 40-50° C. The reaction is finished as soon as no more heat is evolved, and the temperature begins to sink below 40° C, even when not externally cooled. To destroy the excess of dimethyl sulfate the liquid is then heated to boiling with frequent shaking. When it is cold again it is treated with sodium hydroxide till the reaction is alkaline; ether is then added, and after thoroughly shaking in a separating funnel the two layers are separated. The ethereal solution is then dried with anhydrous potassium carbonate, preferably at once by shaking in the funnel, then filtered and warmed on the water-bath till all the ether has evaporated. The residue is purified by fractionation. The boiling point of anisole is 155° C. The yield amounts to 90% of the theory.

Introduction to the preparation of organic compounds, E. Fisher, 90-92, 1909

IUPAC Name

anisole

InChI

InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3

InChI Key

RDOXTESZEPMUJZ-UHFFFAOYSA-N

Canonical SMILES

COC1=CC=CC=C1

MeSH Synonyms

anisol, anisole, methoxybenzene, methyl phenyl ether, phenyl methyl ether

Depositor-Supplied Synonyms

ANISOLE, Methoxybenzene, Methyl phenyl ether, 100-66-3, Benzene, methoxy-, Anisol, Phenyl methyl ether, Phenoxymethane, Anizol, Methoxy-Benzene, 4-methoxybenzene, Benzene, methoxy, Phenol methyl ether, Ether, methyl phenyl, Ether, methyl phenyl-, FEMA Number 2097, NSC 7920, UNII-B3W693GAZH, HSDB 44, FEMA No. 2097, CHEBI:16579, 4-methoxy-benzene, RDOXTESZEPMUJZ-UHFFFAOYSA-N, EINECS 202-876-1, UN2222, AI3-00042, Anisloe, methylphenyl ether, 4-methoxy benzene, Anisole Methoxybenzene, Methoxy-Benzeneanisole, PubChem12830, AC1Q4EAV, AC1Q4FFF, bmse010217, AC1L1OY1, SCHEMBL1205, WLN: 1OR, ACMC-1C6S9, B3W693GAZH, KSC176C8R, SCHEMBL497674, AQUALINE STANDARD 1.0, 296295_ALDRICH, CHEMBL278024, SCHEMBL12015260, 10520_FLUKA, 96109_FLUKA, CTK0H6188, FEMA 2097, NSC7920, METHOXY-BENZENE (ANISOL), MolPort-000-219-450, LABOTEST-BB LTBB002265, LTBB002265, 123226_SIAL, 296295_SIAL, NSC-7920, ANW-14338, AR-1H7389, BDBM50386177, CE0043, EpiMediuM BreviconuM P.E.(Icariin), STL263485, ZINC00897131, AKOS000120161, AS04310, LS-2563, MCULE-2691526560, RP18892, RTR-032978, TRA0007442, UN 2222, Anisole [UN2222] [Flammable liquid], Anisole [UN2222] [Flammable liquid], AN-24560, CJ-04502, I767, OR025028, OR192800, OR192801, ZB015123, DB-003588, TR-032978, A0492, FT-0628309, FT-0652964, C01403, M03556, 14387-EP2272822A1, 14387-EP2316836A1, 19606-EP2269986A1, 19606-EP2269995A1, 19606-EP2270000A1, 19606-EP2272517A1, 19606-EP2272822A1, 19606-EP2272832A1, 19606-EP2275411A2, 19606-EP2281818A1, 19606-EP2281821A1, 19606-EP2284148A1, 19606-EP2284165A1, 19606-EP2284169A1, 19606-EP2287141A1, 19606-EP2287161A1, 19606-EP2287162A1, 19606-EP2289894A2, 19606-EP2289897A1, 19606-EP2289965A1, 19606-EP2292592A1, 19606-EP2292593A2, 19606-EP2292624A1, 19606-EP2298767A1, 19606-EP2298768A1, 19606-EP2298770A1, 19606-EP2298778A1, 19606-EP2298828A1, 19606-EP2301924A1, 19606-EP2301933A1, 19606-EP2301937A1, 19606-EP2301983A1, 19606-EP2305250A1, 19606-EP2305667A2, 19606-EP2305685A1, 19606-EP2305686A1, 19606-EP2308510A1, 19606-EP2308562A2, 19606-EP2308833A2, 19606-EP2308857A1, 19606-EP2308867A2, 19606-EP2308870A2, 19606-EP2308880A1, 19606-EP2308926A1, 19606-EP2308960A1, 19606-EP2309564A1, 19606-EP2311827A1, 19606-EP2314558A1, 19606-EP2314576A1, 19606-EP2314587A1, 19606-EP2314590A1, 19606-EP2314591A1, 37374-EP2311802A1, 37374-EP2311803A1, 56738-EP2277868A1, 56738-EP2277869A1, 56738-EP2277870A1, 56738-EP2292608A1, 56738-EP2295422A2, 56738-EP2298305A1, 56738-EP2298746A1, 56738-EP2298769A1, 56738-EP2308878A2, 56738-EP2371806A1, 56738-EP2371807A1, 56738-EP2380568A1, 187286-EP2272849A1, I01-1977, 3B3-020248, InChI=1/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H

Removed Synonyms

CID7519, ACN-035447, A7048, C060998, ACN-035447 100-66-3, 101221-46-9, 2100-17-6, 489-32-7

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