Pospisil, Jan published the artcileOxidation of catechol. IV. Oxidation of 4-tert-octylcatechol, HPLC of Formula: 1139-46-4, the publication is Chemicke Listy pro Vedu a Prumysl (1958), 939-47, database is CAplus.
cf. C.A. 52, 4546g. Oxidation of 4-tert-octylcatechol (I) (tert-octyl = R = Me3CCH2CMe2) with O or alk. H2O2 gave 2-hydroxy-5-tert-octyl-1,4-benzoquinone (II), also obtained by oxidation of 4-tert-octyl-1,2-benzoquinone (III). The oxidation of I is assumed to proceed through intermediate 1,2,4-trihydroxy-5-tert-octylbenzene (IV) to II. A similar mechanism is proposed for the oxidation of catechol (V) to 2,5-dihydroxy-1,4-benzoquinone (VI). Alkylation of pyrogallol (VII) with di-isobutylene (VIII) gave 5-tert-octylpyrogallol (IX) whose oxidation with Ag2O yielded 6-hydroxy-4-tert-octyl-1,2-benzoquinone (X). Dissolving 110 g. resublimed V in 448 g. hot VIII, treating the solution with 0.2 ml. concentrated H2SO4, stirring the mixture 2.5 hrs. at 105-15°, cooling, filtering off the product with suction, and washing with H2O yielded 167.6 g. I, m. 108° (ligroine). Adding a solution of 4.5 g. I in 220 ml. Et2O to a mixture of 100 ml. Et2O, 5 g. anhydrous Na2SO4, and Ag2O prepared from 135 g. AgNO3, shaking 5 min., filtering, and evaporating gave 4.29 g. III, m. 121-1.5° (Et2O). Acetylation of 2.2 g. I by heating with 6 ml. Ac2O and 0.1 ml. concentrated H2SO4 20 min. on the steam-bath gave 1.8 g. 1,2-diacetoxy-4-tert-octylbenzene, m. 49.5°. The same compound was also obtained by boiling for 10 min. a mixture of 0.44 g. III, 1 g. anhydrous NaOAc, 1.0 g. Zn dust, and 12 ml. Ac2O. To oxidize I, O was passed into a solution of 68 g. KOH in 300 ml. 75% MeOH at a rate of 0.2-0.3 l./min. at 30°. After 15 min., 10 g. I in 100 ml. 75% MeOH was added over a period of 2.5 hrs. The initial blue color turned red. The red clear solution was diluted with 300 ml. H2O, 300 g. ice was added, and the mixture acidified with concentrated HCl. The solution turned yellow and a yellow product precipitated Evaporation of the MeOH in vacuo yielded another crop of II, m. 133.5-4.5° (decomposition) (petr. ether) (7.45 g., 70.1% total). Dissolving 4.5 g. I in 50 ml. 5% solution of KOH in 50% MeOH, treating this solution at 40° with 7 ml. 40% H2O2 for 30 min., stirring the mixture 1.5 hrs., decanting the red solution from resinous material, diluting it to a 10-fold volume with ice and H2O, and acidifying with HCl gave 69.8% II. The same compound was obtained also by oxidation of 0.22 g. III in methanolic solution of KOH (containing 4.5 g. KOH in 45 ml. 75% MeOH) by passing 0.15-0.2 l./min. O through the solution 1.5 hrs. (yield 41.3%) or by treating 0.5 g. III in 2.2 ml. MeOH with 2.5 ml. 40% aqueous KOH and 1.4 ml. 40% H2O2 1 hr. at 40° (yield 15.3%, 0.08 g.). Absorption of II in 0.1N aqueous KOH showed log ε 4.086 at 285 mμ, and log ε 3.216 at 495 mμ. Heating 1 g. II with 5 ml. Ac2O and 0.1 ml. concentrated H2SO4 2 hrs. at 45° and diluting the mixture after 20 hrs. with 20 ml. H2O yielded 0.95 g. 2-acetoxy-5-tert-octyl-1,4-benzoquinone (XI), m. 89.5-90° (petr. ether). Dissolving 0.2 g. XI in 5 ml. Ac2O, adding 0.5 g. Zn dust and 0.5 g. anhydrous NaOAc, refluxing the mixture 30 min., filtering off the Zn, and diluting the filtrate with 25 ml. H2O and 25 g. ice gave 0.22 g. triacetate (XII) of IV, m. 88.5° (petr. ether). The same compound was obtained by treating similarly 2 g. II in 25 ml. Ac2O with 2.5 g. Zn dust and 2.5 g. NaOAc; yield 2.62 g. Hydrogenation of 0.11 g. II in 20 ml. glacial AcOH and 40 ml. Ac2O over PtO2 and heating the mixture with 0.2 ml. concentrated H2SO4 20 min. under H gave XII. If the hydrogenation was carried out in MeOH, the colorless solution of IV formed was reoxidized in contact with air. Heating 30 g. VII with 172 g. VIII and 0.1 ml. concentrated H2SO4 3 hrs. at 105-15° gave 30.7 g. (51.7%) IX, m. 104° (ligroine). Shaking 1.2 g. IX in 100 ml. Et2O with 12 g. Ag2O and 10 g. anhydrous Na2SO4 in 50 ml. Et2O for 10 min. gave a red solution of X whose reductive acetylation by heating with 5 ml. Ac2O, 0.5 g. NaOAc, and 0.5 g. Zn dust in 30 ml. C6H6 gave 1,2,3-triacetoxy-5-tert-octylbenzene, m. 71° (petr. ether). The same compound was also obtained by allowing 0.37 g. III to stand 24 hrs. at 20° with 10 ml. Ac2O and 0.1 ml. H2SO4 or by heating 1 g. IX with 8 ml. Ac2O and 0.1 ml. H2SO4 10 min. on the steam bath (yield 1.25 g.). Heating 0.28 g. VI, 6 ml. Ac2O, and 0.1 ml. H2SO4 2 hrs. at 50° and diluting the mixture after 20 hrs. with ice and H2O gave 0.27 g. 2,5-diacetoxy-1,4-benzoquinone (XIII), m. 151-2° (decomposition) (AcOH). Hydrogenation of 0.14 g. VI in 40 ml. MeOH over PtO2 at 18° gave impure 1,2,4,5-tetrahydroxybenzene whose acetylation with 5 ml. Ac2O and 1 drop H2SO4 gave tetraacetate, m. 226° (AcOH).
Chemicke Listy pro Vedu a Prumysl published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, HPLC of Formula: 1139-46-4.
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