Ra-Cresol

Toluenesulfonic Acid. Toluene reacts readily with fuming sulfuric acid to yield toluene—sulfonic acid. By proper control of conditions, /)i7n7-toluenesulfonic acid is obtained. The primary use is for conversion, by fusion with NaOH, to i ra-cresol. The resulting high purity i7n -cresol is then alkylated with isobutylene to produce 2 (i-dii-tert-huty -para-cmso (BHT), which is used as an antioxidant in foods, gasoline, and mbber. Mixed cresols can be obtained by alkylation of phenol and by isolation from certain petroleum and coal-tar process streams. 

Hopper DJ, PJ Chapman (1971) Gentisic acid and its 3- and 4-methyl-substituted homologues as intermediates in the bacterial degradation of ra-cresol, 3,5-xylenol and 2,4-xylenol. Biochem J 122 19-28. 

Bromcresol green, tetrabromo-ra-cresol-sulfonphthalein (indicator) dissolve 0.1 g in 7.15 mL 0.02 TV NaOH and dilute with water to 250 mL or, 0.1 g in 100 mL 20% alcohol pH range yellow 4.0-5.6 blue. 

Tihe solvent 2,2,2-trifluoroethanol (TFE) is excellent for gel permeation chromatography (GPC) characterization of polyamides and polyacrylates and has many more desirable properties than ra-cresol, the solvent commonly used. The advantages of using TFE rather than... 

Environmental chemicals such as p-nonylphenol (NP), 4-ferf.-octylphenol (OP), 4-ferf.-pentylphenol (TPP), bisphenol-A (BPA), tetrabromobisphenol-A (TBBA), butylbenzylphthalate (BBP), di- -butylphthalate (DBP), butylated hydroxyanisole (BHA), p-chloro-ra-cresol, p-chloro-o-cresol, ds-nonachlor, frans-nonachlor, and the herbicide alachlor [2-chloro-iV-(2,6-diethylphenyl)-N-(methoxymethyl) acetamide] have been discovered to be weakly estrogenic [128,129,137,138]. 

Klara, C.M., Mohamed, R.S., Dempsey, D.M., Holder G.D. (1987) Vapor-liquid equihbria for the binary systems of benzene/toluene, diphenyhnethane/toluene, ra-cresol/l,2,3,4-tetrahydronaphthalene and quinohne/benzene. J. Chem. Eng. Data 32, 143-147. 

Phenol is liable to undergo extensive oxidation during nitration so that carefully controlled conditions are required it forms 40% o- and 13% p-nitrophenolA solvent like chloroform or acetic acid is recommended. The nitration of p-cresol is carried out in benzene and acetic acid solution at 0°, the product being 3-nitro-4-hydroxytoluene (77%). The nitration of ra-cresol is discussed under method 491. Benzene is oxidized and nitrated (oxynitration) to 2,4-dinitrophenoI (72%) or to picric acid (2,4,6-trinitrophenol) by the action of mercuric nitrate in nitric acid. Aromatic alcohols like / -phenylethanol are nitrated as the esters to avoid oxidation products... 

Gopalakrishnan V, Uster P, Rajendran N, Yoshida M. Inhalation safety of phenol and ra-cresol in rodents a fourteen-day repeat dose study. Presented at ISAM congress 2001, Interlaken, Switzerland. 

The neopentyl sulfonate, prepared from the sulfonyl chloride (Pyr, 95% yield), is cleaved nucleophilically under rather severe conditions (Me4NCl, DMF, 160°C, 16 h, 100% yield). These may also be cleaved by acidolysis (CH3CN, H2O, 0.1% TFA, 4-5 days), with LiBr, butanone, reflux, 48 h, or liquid HF, ra-cresol, 100% yield. ... 

CH3SO3H, OT-cresol, CH2CI2. The addition of ra-cresol greatly accelerates the rate of cleavage. ... 

From a phosphorothioate TFMSA, ra-cresol, thiophenol, TFA. These conditions minimized the migration of the benzyl group to the thione. ... 

Fig. 163. Storage modulus, G, and loss tangent, tan 8, measured at 1 Hz, vs temperature for a 40% solution of X7G in ra-cresol. Reproduced from Polymer [Ret 420] by the courtesy of the authors and Elsevier Science Ltd, The Boulevard, Langford Lane, Kidlington 0X51GB, UK...

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