Miller, Ellis’s team published research in Journal of the American Chemical Society in 1938 | CAS: 2525-05-5

4-Butylbenzene-1,2-diol(cas: 2525-05-5) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. Organoboron compounds are less toxic than organostannane reagents, and unlike alkynylzinc and magnesium, many organoboron compounds possess remarkable oxidative and thermal stabilities. Electric Literature of C10H14O2

《Antiseptics. IV. Alkylcatechols》 was published in Journal of the American Chemical Society in 1938. These research results belong to Miller, Ellis; Hartung, Walter H.; Rock, Henry J.; Crossley, Frank S.. Electric Literature of C10H14O2 The article mentions the following:

cf. C. A. 27, 1873. Catechol alkyl ketones were prepared by the Fries rearrangement of the appropriate ester of either catechol (method I) or of guaiacol (method II); in the latter case the reaction is accompanied by simultaneous demethylation. Full details are given of the technic for each method. Pr, m. 139° (II, 23-62% yield); Bu, m. 93-4° (I, 50%); iso-Bu, b4 200-10°, m. 106.5-7.5° (I, 69%); Am, m. 93.8° (I, 72%; II, 30-47%); iso-Am, m. 73-3.5° (I, 60%); hexyl, m. 78-9° (II, 8-17%); heptyl, b5 225°, m. 95.5-6° (I, 50%). In a few cases the 3-isomer, 1,2,3-(HO)2C6H3COR, was isolated in small quantity by fractional crystallization from C6H6, the 4-isomer being less soluble: Et, b5 182-7°, m. 102.5-3.5°; iso-Bu, m. 93-5°; iso-Am, b. 195-205°; heptyl, b4 210-20°, m. 87-8°. Catalytic reduction gives 4-alkylcatechols; Clemmensen reduction gives less satisfactory results. Bu, b5 143-7°, 75% yield, PhOH coefficient 29; Am, b7 158-9°, 86%; iso-Am, b6 155-60°, m. 55.5-8.5°, 70.5%; hexyl, b5 164-9°, PhOH coefficient 129; isohexyl, b5 161-4°; heptyl, b12 195-200°, m. 40°, PhOH coefficient 177; octyl, b5 178°, m. 40°. The experimental part of the paper was very detailed, including the reaction process of 4-Butylbenzene-1,2-diol(cas: 2525-05-5Electric Literature of C10H14O2)

4-Butylbenzene-1,2-diol(cas: 2525-05-5) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. Organoboron compounds are less toxic than organostannane reagents, and unlike alkynylzinc and magnesium, many organoboron compounds possess remarkable oxidative and thermal stabilities. Electric Literature of C10H14O2

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Alcohols – Chemistry LibreTexts