Synthesis of 4-tert-butylphenol

Preparation of 4-tert-butylphenol

Preparation of 4-tert-butylphenol

Preparation of 4-tert-butylphenol

In a 250 ml nickel crucible supported on a tripod a mixture of 120 grams of potassium hydroxide and 5 ml of water are melted by heating over a free flame. When the temperature reaches about 250° C the heating is stopped and without delay while stirring the melt is treated with 50 grams of sodium 4-tert-butylbenzene sulfonate. When the sodium 4-tert-butylbenzene sulfonate is added a stiff and pasty mass is formed, which is heated again over the flame with stirring at 320-330° C for 5-10 minutes. In order to avoid spattering of the hot alkali, particularly when the paste becomes thinner, the melt must be stirred constantly throughout the fusion. There is at first some frothing and as the fusion proceeds and the temperature rises to about 300° the mass suddenly separates to a clear, mobile, brown oil of the potassium salt of 4-tert-butylphenol floating on a pasty, semi-solid mass of alkali. Once the fusion temperature is reached, the reaction is over in about 5 minutes. The melt should not solidify, as it becomes very difficult to handle. The content of the crucible in small portions is poured into a 1.5 liter beaker half filled with crushed ice. When the melt has been dissolved in water the alkaline solution is poured into a long-necked flask suitable for steam distillation. The solution is acidified with hydrochloric acid and steamed distilled. 4-tert-butylphenol separates as a solid on cooling and may lodge in the condenser. To prevent it from clogging a flow of cold water through the condenser is stopped. The 4-tert-butylphenol is obtained as a crystalline mass, which is dried, purified by crystallization from petroleum ether. The yield of 4-tert-butylphenol is 18-20 g, with melting point 98.5° C.

Experiments in Organic Chemistry, L. F. Fieser, 182, 1941

IUPAC Name

4-tert-butylphenol

InChI

InChI=1S/C10H14O/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7,11H,1-3H3

InChI Key

QHPQWRBYOIRBIT-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

4-(t-butyl)phenol, 4-tert-butylphenol, 4-tertiary-butylphenol, butylphen, p-tert-butylphenol, para-tertiary-butylphenol

Depositor-Supplied Synonyms

4-tert-Butylphenol, p-tert-Butylphenol, Butylphen, 98-54-4, 4-(tert-Butyl)phenol, 4-(1,1-Dimethylethyl)phenol, PTBP, 4-t-Butylphenol, Phenol, p-tert-butyl-, p-t-Butyl phenol, Phenol, 4-(1,1-dimethylethyl)-, p-t-Butylphenol, p-terc.Butylfenol, 4-tert-butyl-phenol, 1-Hydroxy-4-tert-butylbenzene, para-tertiary-butylphenol, Phenol, p-(tert-butyl)-, 4-Tert-Butylpheno, CHEBI:34444, Ucar butylphenol 4-T, Caswell No. 130E, NSC 3697, p-terc.Butylfenol [Czech], Ucar butylphenol 4-T flake, CHEMBL16217, QHPQWRBYOIRBIT-UHFFFAOYSA-N, EINECS 202-679-0, SBB060742, EPA Pesticide Chemical Code 064113, NCGC00159377-02, NCGC00159377-04, AI3-00126, DSSTox_CID_221, DSSTox_RID_75442, DSSTox_GSID_20221, CAS-98-54-4, p-tertbutylphenol, 4tert-butylphenol, para-t-butylphenol, 4- t-butylphenol, 4-t-butyl phenol, 4-tret-Butylphenol, p-tert-butyl phenol, 4- tert-butylphenol, 4-tert-butyl phenol, 4-tert.-butylphenol, p-tertiary butylphenol, 4-tert.-butyl phenol, 4-tert.-butyl-phenol, paratert.-butyl phenol, para-tert. butyl phenol, para-tert.-butyl phenol, para-tertiary butylphenol, Phenol, 4-tert-butyl-, AC1L1ONS, AC1Q1MFG, para-tertiary-butyl phenol, Epitope ID:119706, UNII-O81VMW36CV, AC1Q1M8O, O81VMW36CV, PARA-TERT-BUTYLPHENOL, SCHEMBL19157, B99901_ALDRICH, KSC486O7J, BIDD:ER0239, W391808_ALDRICH, 425761_ALDRICH, 506761_SUPELCO, 4-TERTIARY BUTYL PHENOL, CTK3I6774, FEMA 3918, QHPQWRBYOIRBIT-UHFFFAOYSA-, NSC3697, MolPort-001-789-043, LABOTEST-BB LTBB002519, NSC-3697, Tox21_111617, Tox21_202326, Tox21_300103, ANW-50107, AR-1I1413, BBL018706, STK397447, ZINC01666982, AKOS000119700, Tox21_111617_1, AS00221, LS-7244, MCULE-9877285241, RP21408, RTR-030674, TRA0092036, WLN: QR DX1 & 1 & 1, NCGC00159377-03, NCGC00159377-05, NCGC00159377-06, NCGC00254213-01, NCGC00259875-01, AJ-29057, AK-72998, AN-24485, BR-72998, CJ-06070, CJ-27016, K768, KB-40468, SC-22420, 4-(1,1-DIMETHYL-1-ETHYL)PHENOL, DB-080546, ST2411041, TR-030674, AM20050202, B0230, B0735, FT-0688077, ST50586213, C14200, M-6037, Phenol, 4-(1,1-dimethylethyl)-, homopolymer, AE-562/40191182, I01-8840, 3B3-032706, InChI=1/C10H14O/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7,11H,1-3H3, 30813-81-1

Removed Synonyms

Terbutol, p-sec-Butylphenol, 2-TERT-BUTYLPHENOL, 4-tertiary-butylphenol, Phenol,1-dimethylethyl)-, 4-(T-BUTYL)PHENOL, Phenol, (1,1-dimethylethyl)-, CID7393, C006862, 27178-34-3, 6268-05-9

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