Synthesis of p-toluic acid (4-methylbenzoic acid; 4-toluic acid)

Preparation of p-toluic acid

Preparation of p-toluic acid (4-methylbenzoic acid; 4-toluic acid)

Preparation of p-toluic acid (4-methylbenzoic acid; 4-toluic acid)

5 g of p-tolunitrile, 75 ml of 10% aqueous sodium hydroxide solution and 15 ml of ethanol are mixed and boiled under a reflux. The ethanol serves in preventing the p-tolunitrile, which volatilizes in the steam, from crystallizing in the condenser. After 1 hour of boiling the solution becomes clear, but the hydrolysis is fully complete after 1.5 hours of boiling. Then the solution is cooled and neutralized by adding concentrated hydrochloric acid until precipitation of p-toluic acid is complete. The crystals of p-toluic acid are collected by filtration, washed well with cold water and dried yielding about 5.5 g of crude product. Further p-toluic acid is purified by crystallization from equal volumes of water and ethanol yielding product, which melts at 178° C.

Practical organic chemistry, by F. G. Mann, 195, 1960

IUPAC Name

4-methylbenzoic acid

InChI

InChI=1S/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10)

InChI Key

LPNBBFKOUUSUDB-UHFFFAOYSA-N

Canonical SMILES

CC1=CC=C(C=C1)C(=O)O

MeSH Synonyms

4-methylbenzoate, 4-toluic acid, 4-toluic acid, barium salt, 4-toluic acid, cadmium salt, 4-toluic acid, calcium salt, 4-toluic acid, potassium salt, 4-toluic acid, zinc salt, p-methylbenzoate, p-toluenecarboxylate, p-toluic acid

Depositor-Supplied Synonyms

4-Methylbenzoic acid, P-TOLUIC ACID, 4-Toluic acid, p-Methylbenzoic acid, 99-94-5, Crithminic acid, Benzoic acid, 4-methyl-, p-Toluylic acid, p-Carboxytoluene, para-Toluic acid, 4-Methyl-Benzoic Acid, Toluate, p-toluicacid, Toluenecarboxylic acid, NSC 2215, UNII-A26GBX5SSV, CHEBI:36635, LPNBBFKOUUSUDB-UHFFFAOYSA-N, EINECS 202-803-3, BRN 0507600, AI3-15627, AB-131/40170882, 4MA, para toluic acid, 4-Carboxytoluene, 4-methylbenzic acid, p-methyl benzoic acid, p-Tolylcarboxylic acid, para-methylbenzoic acid, 4-Methyl benzoic acid, PubChem15433, ACMC-209sek, AC1Q2JXU, AC1Q2QRL, toluene-4-carboxylic acid, A26GBX5SSV, DSSTox_CID_1618, bmse000414, AC1L1OU1, WLN: QVR D1, DSSTox_RID_76238, NCIOpen2_001271, DSSTox_GSID_21618, SCHEMBL93638, SUPPORTED BENZOIC ACID, T36803_ALDRICH, 4-methylbenzenecarboxylic acid, KSC487C8N, CHEMBL21708, RARECHEM AL BO 0067, 89902_FLUKA, CTK3I7186, TIMTEC-BB SBB040516, NSC2215, 2420-97-5 (cadmium salt), MolPort-000-631-743, 23292-93-5 (zinc salt), 67874-52-6 (barium salt), NSC-2215, AKOS BBS-00003712, Tox21_201091, ANW-41082, AR-1L2554, BBL005649, KM3522, LABOTEST-BB LT00798642, SBB040516, STK498227, AKOS000119644, AC-3061, AS00864, BS-3777, LS-2071, MCULE-2497536187, RP20258, CAS-99-94-5, OTAVA-BB 7119561590, NCGC00091128-01, NCGC00091128-02, NCGC00258643-01, AJ-19289, AK106262, AN-13376, BC675261, KB-72731, TR-033307, FT-0654542, ST24023609, ST50213865, C01454, 31538-EP2308858A1, 31538-EP2311816A1, 31538-EP2311817A1, I04-0389, 3B3-032781, UNII-I889W3548N component LPNBBFKOUUSUDB-UHFFFAOYSA-N, InChI=1/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10, 852148-36-8

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