Synthesis of 4-methoxybenzoic acid

Preparation of 4-methoxybenzoic acid

Preparation of 4-methoxybenzoic acid

Preparation of 4-methoxybenzoic acid

The 1 mole of 4-hydroxybenzoic acid 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 solid reaction product is isolated by filtration, washed with water, and recrystallized from the mixture of alcohol and water. Unchanged 4-hydroxybenzoic acid can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 4-hydroxybenzoic acid is 75% m.p. 183-185 °C;

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

IUPAC Name

4-methoxybenzoic acid

InChI

InChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)

InChI Key

ZEYHEAKUIGZSGI-UHFFFAOYSA-N

Canonical SMILES

COC1=CC=C(C=C1)C(=O)O

MeSH Synonyms

4-anisic acid, 4-anisic acid, 14C-carboxy, 4-anisic acid, copper (+2) salt, 4-anisic acid, potassium salt, 4-anisic acid, sodium salt, 4-methoxybenzoate, p-anisic acid, para-anisic acid

Depositor-Supplied Synonyms

4-METHOXYBENZOIC ACID, p-Anisic acid, 100-09-4, p-Methoxybenzoic acid, ANISIC ACID, 4-Anisic acid, Draconic acid, Benzoic acid, 4-methoxy-, 4-Methoxybenzoate, ANISIC ACID, PARA, 4-methoxy-benzoic acid, p-methoxybenzoate, Methoxybenzoic acid, Anisic acid, p-isomer, 4-Methoxy benzoic acid, P-Methoxy Benzoic Acid, Kyselina 4-methoxybenzoova, UNII-4SB6Y7DMM3, CHEBI:40813, ZEYHEAKUIGZSGI-UHFFFAOYSA-N, Kyselina 4-methoxybenzoova [Czech], EINECS 202-818-5, NSC 32742, BRN 0508910, AI3-00893, 73424-02-9, AE-848/32075009, ANN, 1335-08-6, para-anisic acid, 4-Carboxyanisole, 4-methoxybenzoicacid, 4-methoxylbenzoic acid, PubChem23856, 1sv3, paramethoxy benzoic acid, ACMC-1BLVJ, AC1L1OUP, ANISIC ACID(P-), 4-(methyloxy)benzoic acid, ANISIC ACID, 4-, bmse000356, bmse010012, AC1Q4A1W, 4SB6Y7DMM3, NCIOpen2_004706, SCHEMBL43335, CHEMBL21932, W394505_ALDRICH, 536-45-8 (sodium), 117390_ALDRICH, Jsp000058, RARECHEM AL BO 0059, SCHEMBL12015259, 10550_FLUKA, 84688_FLUKA, FEMA 3945, HMDB01101, TIMTEC-BB SBB037872, 52509-81-6 (potassium), NSC7926, MolPort-000-871-566, OTAVA-BB 1779304, P-METHYLHYDROXYBENZOIC ACID, HMS1760M22, HMS3604D05, ZINC332748, NSC-7926, NSC32742, STR02874, AKOS BBS-00003715, EINECS 215-618-8, AB2885, ANW-14157, HTS006404, LABOTEST-BB LT00781808, LABOTEST-BB LT03327667, LABOTEST-BB LT03330798, NSC-32742, SBB037872, STK498216, 4-Methoxybenzoic acid; p-Anisic acid, 73424-02-9 (copper+2), AKOS000118883, AM86179, AS00727, AS03913, DB02795, LS11457, MCULE-7627915900, PS-3382, TRA0034183, AC-11353, AJ-19560, AK-41188, AN-24541, BP-10768, KB-74695, LS-20071, OR034330, OR156327, OR192138, OR192139, OR192140, OR192141, SC-16070, ST080859, AB1002335, DB-023671, RT-001038, TL8006996, A0482, FT-0658638, FT-0671155, ST24032813, C02519, M-5859, 31543-EP2308858A1, 31543-EP2311816A1, 31543-EP2311817A1, 4-10-00-00346 (Beilstein Handbook Reference), 3B4-1130, I01-1731, Q-200489, T0518-6049, InChI=1/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10

Removed Synonyms

4-Mercaptobenzoic acid, Benzoic acid, methoxy-, C8H8O3, CID7478, ‘LGC’ (2407)

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