Synthesis of 4-methoxyphenol

Preparation of 4-methoxyphenol

Preparation of 4-methoxyphenol

Preparation of 4-methoxyphenol

The 1 mole of hydroquinone (benzene-1,4-diol, quinol) 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 per acid group. 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 solid reaction product is isolated by filtration, washed with water, and recrystallized from petroleum ether or vacuum distilled b.p. 128°C/12mm. Unchanged hydroquinone can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 4-methoxyphenol is 60%, b.p. 243 °C; b.p. 128°C/12mm; mp.p 55-57 °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-hydroxyanisole, 4-hydroxyanisole, potassium salt, 4-hydroxyanisole, sodium salt, 4-methoxyphenol, hydroquinone methyl ether, hydroquinone monomethyl ether, Leucodinine B, mequinol, p-hydroxyanisole, para-methoxyphenol

Depositor-Supplied Synonyms

4-Methoxyphenol, Mequinol, 150-76-5, 4-Hydroxyanisole, p-Hydroxyanisole, p-Methoxyphenol, HYDROQUINONE MONOMETHYL ETHER, Phenol, 4-methoxy-, Leucodine B, P-Guaiacol, MEHQ, Leucobasal, Mechinolum, Novo-Dermoquinona, HQMME, Hydroquinone methyl ether, Phenol, p-methoxy-, 1-Hydroxy-4-methoxybenzene, para-methoxyphenol, PMF (antioxidant), USAF AN-7, Monomethyl ether hydroquinone, p-Hydroxymethoxybenzene, 4-Methoxy-phenol, Mechinolo [DCIT], NSC 4960, Mequinolum [INN-Latin], UNII-6HT8U7K3AM, BMS 181158, BMS-181158, 6HT8U7K3AM, Mono methyl ether hydroquinone, 4-Hydroxyphenol, polymer-bound, CCRIS 5531, CHEBI:69441, HSDB 4258, NSC4960, NWVVVBRKAWDGAB-UHFFFAOYSA-N, EINECS 205-769-8, MFCD00002332, SBB060425, NCGC00091390-02, AI3-00841, DSSTox_CID_828, DSSTox_RID_75814, DSSTox_GSID_20828, Leucodinine B, CAS-150-76-5, Leucobasalreg, Mequinolum, Mechinolo, 4methoxyphenol, paramethoxyphenol, 4-methoxylphenol, p- methoxyphenol, p-methoxy phenol, p-methoxy-phenol, 4-methoxy phenol, Eastman HQMME, Mequinol (INN), 4-(methoxy)phenol, para- hydroxyanisole, 4-(methyloxy)phenol, PubChem2276, hydroquinone methylether, Mequinol [INN:DCF], ACMC-1BYTI, Mequinol (USAN/INN), AC1Q4DHN, AC1Q4FEL, PHENOL,4-METHOXY, CHEMBL544, NCIMech_000709, AC1L1S4S, WLN: QR DO1, SCHEMBL21009, M18655_ALDRICH, Mequinol [USAN:INN:DCF], KSC174Q4B, MLS002454409, 650382_ALDRICH, GTPL6827, ZINC1684, Jsp002874, SCHEMBL12015251, 54050_FLUKA, BDBM36295, CTK0H4840, MolPort-000-145-974, 1122-93-6 (potassium salt), HMS2270F04, HMS3264P13, Pharmakon1600-00212037, NSC-4960, Tox21_111125, Tox21_202367, Tox21_302876, ANW-21297, AR-1J3939, BBL019135, CCG-35855, LS-877, NSC760357, ZINC00001684, AKOS000119852, Tox21_111125_1, AC-3292, AS04576, CS22939, LS10474, MCULE-7494596350, NSC-760357, PS-3375, RP19570, RTR-006165, TRA0003513, TRA0097808, NCGC00091390-01, NCGC00091390-03, NCGC00091390-04, NCGC00256552-01, NCGC00259916-01, AJ-08066, AK-46469, AN-13109, BR-46469, HQMME; HYDROXYQUINONE METHYL ETHER, KB-39632, NCI60_004190, OR025495, SMR001252253, TL806296, ZB000389, AB1001999, DB-003965, ST2411512, TR-006165, FT-0082705, FT-0618865, M0123, ST51046605, AZ0001-0119, 5566-EP2269977A2, 5566-EP2275413A1, 5566-EP2284157A1, 5566-EP2287156A1, 5566-EP2298750A1, 5566-EP2305648A1, 5566-EP2311811A1, 5566-EP2371803A1, 5566-EP2377843A1, D04926, EC 205-769-8, M-5917, 46863-EP2299326A1, 46863-EP2311804A2, A809071, I01-2543, Q-200491, 4-Hydroxyanisole; Hydroquinone monomethyl ether; MEHQ, 3B3-032693, S4077,150-76-5, 4-Methoxybenzyl S-(4,6-dimethylpyrimidin-2-yl)thiocarbonate, InChI=1/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H, HYDROQUINONE MONOMETHYL ETHER(SEE ALSO: HYDROQUINONE DIETHYL ETHER (CAS 150-78-7))

Removed Synonyms

Solage, Methoxyphenol, Mixture Name, Solage (Salt/Mix), ”para”-Guaiacol, 4-Methoxycyclohexanol, MENTHYL ANTHRANILATE, 4-MP, C7H8O2, 4-hydroxyanisole, sodium salt, 4-hydroxyanisole, potassium salt, CID9015, C009760, MME, 1530-05-8, 4HA

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