Synthesis of 3-methoxyphenol

Preparation of 3-methoxyphenol

Preparation of 3-methoxyphenol

Preparation of 3-methoxyphenol

The 1 mole of resorcinol 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 resorcinol can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 3-methoxyphenol is 50%, b.p. 113-115 °C/5 mm; b.p. 144°C/25mm; n20/D 1.552; d=1.131 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

3-methoxyphenol

InChI

InChI=1S/C7H8O2/c1-9-7-4-2-3-6(8)5-7/h2-5,8H,1H3

InChI Key

ASHGTJPOSUFTGB-UHFFFAOYSA-N

Canonical SMILES

COC1=CC=CC(=C1)O

MeSH Synonyms

3-hydroxyanisole, 3-methoxyphenol

Depositor-Supplied Synonyms

3-METHOXYPHENOL, 150-19-6, m-Methoxyphenol, 3-Hydroxyanisole, m-Hydroxyanisole, Phenol, 3-methoxy-, m-Guaiacol, Resorcinol monomethyl ether, 1-Hydroxy-3-methoxybenzene, Resorcinol methyl ether, Phenol, m-methoxy-, 3-methoxy phenol, 3-(methyloxy)phenol, 3-METHOXY-PHENOL, 3-Hydroxyanisol, NSC 21735, UNII-HXB7441U87, CHEBI:52678, ASHGTJPOSUFTGB-UHFFFAOYSA-N, HXB7441U87, EINECS 205-754-6, 4-METHOXYPHEOL, HYDROXYANISOLE-4, AI3-00796, META-METHOXYPHENOL, METHOXYPHENOL(P-), PARA METHOXY PHENOL, METHOXYPHENOL, PARA-, AKOS AKM01253, PARAGOS 500026, 1-HYROXY-4-METHOXYBENZENE, OTAVA-BB 1366571, LABOTEST-BB LTBB001936, LABOTEST-BB LTBB002880, m-Hydroxyanisol, methyl resorcinol, m-methoxy-phenol, 3-methyloxyphenol, zlchem 218, PubChem13577, AC1Q7AKN, DSSTox_CID_2012, DSSTox_GSID_22012, SCHEMBL28256, KSC177G7R, CHEMBL57891, ACMC-209d43, 328456_ALDRICH, AC1L1S44, AC1Q4E80, Jsp002861, SCHEMBL12015261, BDBM36297, CTK0H7378, ZLC0026, MolPort-001-785-031, BB_SC-6850, ZINC389516, NSC21735, Tox21_303820, ANW-21265, AR-1F4053, BBL009702, CK1184, MFCD00002267, NSC-21735, SBB060932, STL141067, ZINC00389516, AKOS000120300, AS00218, AS04315, CS18747, MCULE-7145223398, RP19573, RTR-006122, NCGC00357098-01, 4CN-1025, AC-18515, AJ-20809, AK105946, AN-44011, CAS-150-19-6, KB-32557, L543, OR010963, OR156045, SC-06352, SC-27007, ZB011737, DB-002515, LS-104768, ST2410764, TR-006122, FT-0616005, M0122, ST51047026, X-1701, 88189-EP2269977A2, 88189-EP2270006A1, 88189-EP2277881A1, 88189-EP2298750A1, 88189-EP2305648A1, I01-7331, W-108077, 3B3-032664, InChI=1/C7H8O2/c1-9-7-4-2-3-6(8)5-7/h2-5,8H,1H

Removed Synonyms

Leucobasal, Mechinolum, Mequinol, p-Methoxyphenol, p-Hydroxyanisole, 4-Methoxyphenol, Leucodine B, P-Guaiacol, 4-Hydroxyanisole, Novo-Dermoquinona, 3-Anise alcohol, O-methylhydroquinone, HQMME, MEHQ, p-Hydroxymethoxybenzene, Hydroquinone methyl ether, 1-Hydroxy-4-methoxybenzene, Monomethyl ether hydroquinone, C7H8O2, CID9007, HYDROQUINONE MONOMETHYL ETHER, C094702, 6971-51-3, 152423-09-1

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