Synthesis of 4-hydroxybenzoic acid

Preparation of 4-hydroxybenzoic acid

Preparation of 4-hydroxybenzoic acid

Preparation of 4-hydroxybenzoic acid

p-Cresol is converted into potassium cresyl sulphate by treating 1 mole of cresol (as concentrated solution) at 60-70° C with 1.5 mole of potassium pyrosulphate for eight to ten hours. The potassium salt is then dissolved by warming with an equal weight of potassium hydroxide dissolved in a little water. The solution is heated on the water-bath, and rather more than the calculated quantity (one mole) of potassium permanganate in 4%, solution slowly added, and the whole heated for some hours. Excess of permanganate is then destroyed by adding a few drops of alcohol and continuing the heating until a filtered sample no longer shows a pink colour. The whole is filtered hot, the filtrate acidified with hydrochloric acid, and then warmed on the water-bath to hydrolyse the sulphuric ester. On cooling, the greater part of the 4-hydroxybenzoic acid crystallises out and the rest is extracted with ether. After recrystallisation from water it melts at 210° C. The yield is almost theoretical.

Preparation of organic compounds, E. de. Barry Barnett, 160, 1912

IUPAC Name

4-hydroxybenzoic acid

InChI

InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)

InChI Key

FJKROLUGYXJWQN-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1C(=O)O)O

MeSH Synonyms

4-hydroxybenzoate, 4-hydroxybenzoic acid, 4-hydroxybenzoic acid, calcium salt, 4-hydroxybenzoic acid, copper(2+)(1:1) salt, 4-hydroxybenzoic acid, dilithium salt, 4-hydroxybenzoic acid, dipotassium salt, 4-hydroxybenzoic acid, disodium salt, 4-hydroxybenzoic acid, monopotassium salt, 4-hydroxybenzoic acid, monosodium salt, 4-hydroxybenzoic acid, monosodium salt, 11C-labeled, p-hydroxybenzoate, para-hydroxybenzoic acid, sodium p-hydroxybenzoate tetrahydrate

Depositor-Supplied Synonyms

4-HYDROXYBENZOIC ACID, p-Hydroxybenzoic acid, 99-96-7, 4-Carboxyphenol, Benzoic acid, 4-hydroxy-, p-Salicylic acid, p-carboxyphenol, Benzoic acid, p-hydroxy-, para-Hydroxybenzoic acid, Paraben-acid, 4-hydroxy-benzoic acid, 4-Hydroxybenzoesaeure, p-hydroxy-Benzoic acid, p-Salicylate, p-Oxybenzoesaure [German], p-Salicyclic Acid, p-hydroxy-Benzoate, 4-hydroxy-benzoate, 4-Hydroxy-benzoesaeure, 4-hydroxy benzoic acid, Acido p-idrossibenzoico [Italian], Hydroxybenzoic acid, Kyselina 4-hydroxybenzoova [Czech], NSC 4961, Kyselina 4-hydroxybenzoova, Hydroxybenzenecarboxylic acid, UNII-JG8Z55Y12H, Acetysalicyclic acid impurity A, CHEMBL441343, CHEBI:30763, HSDB 7233, HYDROXYBENZOIC ACID, PARA, FJKROLUGYXJWQN-UHFFFAOYSA-N, EINECS 202-804-9, 3pcc, 3pch, AI3-01003, DSSTox_CID_6647, DSSTox_RID_78173, DSSTox_GSID_26647, Benzoic acid, p-hydroxy, Benzoic acid, 4-hydroxy, WLN: QVR DQ, 4-HBA, H20059_ALDRICH, W398608_ALDRICH, 240141_ALDRICH, CAS-99-96-7, NSC4961, DB04242, NCGC00166040-01, C00156, p-Salicylicacid, AE-848/32195059, p-Oxybenzoesaure, 4-Hydroxybenzoicacid, 4-hyroxybenzoic acid, PHBA, parahydroxybenzoic acid, phenol derivative, 8, 4-hydroxylbenzoic acid, p-hydroxy benzoic acid, p-hydroxybenzoate ester, Acido p-idrossibenzoico, 4-hydroxybenzoi c acid, PubChem16819, p-hydroxybenzoate esters, ACMC-209sel, 4-hydroxybenzoate esters, 4-hydroxyl benzoic acid, 4-Hydroxybenzoate, III, bmse000092, bmse000583, AC1Q73EU, SCHEMBL4110, KSC173K8H, BIDD:ER0706, 4-Hydroxybenzenecarboxylic acid, AC1L18K3, AC1Q1H26, CCRIS 8812, JG8Z55Y12H, BDBM26194, CHEBI:79323, HMDB00500, MolPort-000-871-606, BB_NC-2308, LR-68, ZINC332752, NSC-4961, Tox21_202342, Tox21_303301, AC-008, ANW-41083, AR-1K9747, BBL011981, DNC008509, SBB040549, STL138745, AKOS000119033, 114-63-6 (mono-hydrochloride salt), AM87513, MCULE-1367764897, NE10208, RP20404, RTR-007731, TRA0058557, 16782-08-4 (mono-potassium salt), NCGC00166040-02, NCGC00257058-01, NCGC00259891-01, 4CN-0919, AJ-19561, AK106263, AN-16204, BC228180, KB-39154, LS-37525, OR034017, OR182934, OR383012, SC-16333, AB1002080, ST2411467, FT-0618695, ST50210584, 44643-EP2281819A1, 44643-EP2292619A1, 44643-EP2298735A1, 44643-EP2305659A1, 44643-EP2311809A1, 44643-EP2311818A1, 194587-EP2371808A1, 3B4-0183, 46DD083D-BFD3-4CE1-B2D9-6C6D5FEFD3D9, I04-1478, I14-7358, J-660066, W-100004, BENZOIC-CARBOXY-13C ACID, 4-HYDROXY- (9CI), InChI=1/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10

Removed Synonyms

4-hydroxybenzoate, Paraben, p-hydroxybenzoate, null, CID135, 4-Hydroxycyclohexanecarboxylic acid, 4-hydroxybenzoic acid, calcium salt, sodium p-hydroxybenzoate tetrahydrate, 4-hydroxybenzoic acid, disodium salt, 4-hydroxybenzoic acid, dilithium salt, 4-hydroxybenzoic acid, monosodium salt, 4-hydroxybenzoic acid, dipotassium salt, 4-hydroxybenzoic acid, monopotassium salt, H0207, 4-hydroxybenzoic acid, copper(2+)(1:1) salt, C038193, 4-hydroxybenzoic acid, monosodium salt, 11C-labeled, 17419-81-7, PHB, 105-56-6, 114-63-6, 72702-76-2

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