Synthesis of 3,4,5-trimethoxybenzoic acid

Preparation of 3,4,5-trimethoxybenzoic acid

Preparation of 3,4,5-trimethoxybenzoic acid

Preparation of 3,4,5-trimethoxybenzoic acid

The 1 mole of 3,4,5-trihydroxybenzoic acid is treated rapidly with stirring, in a three-necked flask provided with a reflux condenser, stirrer, internal thermometer, and dropping funnel, with 3.75 mole of 10% sodium hydroxide. With vigorous stirring, 3 mole of dimethyl sulfate are 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 3,4,5-trihydroxybenzoic acid can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 2-methylanisole is 70%, m.p. 168-171 °C; b.p. 225-227 °C/10 mm;

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

IUPAC Name

3,4,5-trimethoxybenzoic acid

InChI

InChI=1S/C10H12O5/c1-13-7-4-6(10(11)12)5-8(14-2)9(7)15-3/h4-5H,1-3H3,(H,11,12)

InChI Key

SJSOFNCYXJUNBT-UHFFFAOYSA-N

Canonical SMILES

COC1=CC(=CC(=C1OC)OC)C(=O)O

MeSH Synonyms

3,4,5-trimethoxybenzoic acid, 3,4,5-trimethoxybenzoic acid, potassium salt, 3,4,5-trimethoxybenzoic acid, sodium salt

Depositor-Supplied Synonyms

3,4,5-TRIMETHOXYBENZOIC ACID, 118-41-2, Eudesmic acid, Gallic acid trimethyl ether, Tri-O-methylgallic acid, Trimethylgallic acid, Veratric acid, 5-methoxy-, Benzoic acid, 3,4,5-trimethoxy-, UNII-V5C9H0SC9F, 3,4,5-trimethoxy-benzoic acid, 3,4,5-Trimethoxy Benzoic Acid, CHEBI:454991, NSC2525, SJSOFNCYXJUNBT-UHFFFAOYSA-N, NSC 2525, PubChem11527, Spectrum_000082, 5-methoxy-veratric acid, SpecPlus_000919, AC1L1QTQ, Spectrum2_000791, Spectrum3_000260, Spectrum4_001625, Spectrum5_000409, 3,5-Trimethoxybenzoic acid, AC1Q5TS4, SCHEMBL6592, V5C9H0SC9F, Oprea1_180796, BSPBio_001680, CBDivE_013176, CBDivE_014084, KBioGR_002029, KBioSS_000502, T69000_ALDRICH, KSC179I3J, MLS002207176, DivK1c_007015, SPBio_000922, ACMC-2099×1, Benzoic acid,4,5-trimethoxy-, AC1Q47N5, CHEMBL377172, 3,4,5 trimethoxy benzoic acid, RARECHEM AL BO 0027, BDBM92458, CTK0H9434, KBio1_001959, KBio2_000502, KBio2_003070, KBio2_005638, KBio3_001180, MolPort-000-871-568, OTAVA-BB 1312859, BB_NC-2273, ZINC347833, AKOS 214-77, NSC-2525, STR02399, EINECS 204-248-2, ANW-17123, AR-1E8926, BBL009652, CCG-40169, LABOTEST-BB LT00454915, LABOTEST-BB LT03331418, MFCD00002501, SBB058083, STK246307, AKOS000113542, AC-2858, AM86360, AS00730, MCULE-4509330001, PS-7989, RL00705, RP26670, RTR-003158, TRA0053930, NCGC00179094-01, 4CN-2742, AJ-20064, AK-47760, AN-13524, BT000282, OR027145, OR152471, SMR000112093, ST097622, AB1002356, AI3-21153, ST2404571, A-7628, A15148, Gallic acid trimethyl ether; Trimethylgallic acid, I01-1324, Q-200337, T5883834, 3B3-082078, Hydrogen(T-4)-bis[3,5-bis(1,1-dimethylethyl)-2-hydroxybenzoato(2-)-O1, O2]aluminate(1-), 1195674-42-0

Removed Synonyms

Asaronic acid, 3,3′-Thiodipropionic acid, CID8357, C10H12O5, 2,3,4-TRIMETHOXYBENZOIC ACID, T0705, 573-11-5, 59042-88-5

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