Sheiman, B. M. published the artcileSynthesis of alkylphenols from borates by the Friedel-Crafts reaction, Related Products of catalysis-chemistry, the publication is Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya (1960), 876-80, database is CAplus.
Two preparations of alkylphenols from sym. boric esters [trialkyl borates and triphenyl borate(I)] in the presence of AlCl3, and through a preliminary preparation of mixed boric esters were given. The yields reached 70-98% and the alkylphenols obtained did not contain nonphenolic compounds A mixture of 23 g. tributyl borate, 18.8 g. PhOH, and 0.2 g. PhONa was heated to 200-30¡ã (maintaining the temperature of BuOH below 120-30¡ã) to yield 14.8 g. BuOH [i.e., the theoretical amount, assuming the formation of (PhO)2BOBu (II)], n20D 1.4000. To a mixture of 1 g. II in 200 ml. pyridine was added, portionwise, with cooling, 52 g. freshly sublimed AlCl3. The mixture heated 15-20 min. to 80¡ã and 15 min. at 80-5¡ã, poured into a mixture of ice and HCl, and extracted with Et2O, and the phenols extracted with 10% NaOH and treated as usual gave 80% mixture of o- and p-butylphenol, b5.5 92-106¡ã, further fractionated to yield 11.6% o-sec-butylphenol, b6.5 92.5¡ã, n20D 1.5228, d20 0.9876, MRD 46.42 (o-sec-butylphenoxyacetic acid m. 109.5-110¡ã; the toluide m. 69.5-70.5¡ã) and 81.2% p-sec-butylphenol, b6.5 105.5¡ã, m. 57-7.5¡ã (petr. ether), n20D 1.5200, d20 0.9787, MRD 46.59 (the toluidide of p-sec-butylphenoxyacetic acid m. 90-1¡ã). In an analogous manner, 58 g. I and 18.8 g. triisopropyl borate dissolved in 150 ml. ligroine and 52 g. AlCl3 yielded a fraction b10 99-120¡ã, further fractionated to yield o-isopropylphenol, b2.5 67-7.5¡ã, n20D 1.5282, d20 1.0127, MRD 41.43. Propyl diphenyl borate was obtained by the simultaneous esterification of 18 g. PrOH and 56.4 g. phenol with 18.6 g. boric acid in 80 ml. toluene in a Dean-Stark apparatus; after distillation of PhCH3 and the unreacted phenol in vacuo (water-jet pump), 150 ml. ligroine and 52 g. AlCl3 were added, and the mixture treated as above to yield 73% propylphenol isomers, b10 103-4¡ã, n20D 1.5253, d20 0.9972, MRD 41.88; the phenoxyacetic acid m. 63-5¡ã; phenylurethan m. 77-85¡ã. A mixture of 76.7 g. triisobutyl borate, 193.4 g. I dissolved in 450 ml. ligroine, and 133.5 g. AlCl3 was heated 2 hrs. at 35-60¡ã and about 1 hr. at 85-90¡ã, and treated as usual to yield 70% p-tert-butylpbenol, b5 99-9.5¡ã, m. 98.5-99¡ã (petr. ether); (the phenoxyacetic acid m. 85.5-86¡ã) and 2 high-boiling fractions of polyalkyl phenols b5 120-30¡ã (10.3 g.), and b5 150-65¡ã (4 g.). I (58 g.) and 30.8 g. tricyclohexyl borate 100 ml. ligroine heated 30 min. at 90¡ã with 40 g. AlCl3 yielded 42.2% p-cyclohexylphenol b11 1.50-3¡ã, m. 127.5-8¡ã (benzene); benzoate derivative m. 114-14.5¡ã (alc.). The nonphenolic part yielded 10.8 g. of a fraction, b6 101-3¡ã, n20D 1.5283, d20 0.9586, and 6.2 g. of a fraction b6 178-80¡ã, n20D 1.5432. 27 references.
Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya published new progress about 1798-04-5. 1798-04-5 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(4-(tert-Butyl)phenoxy)acetic acid, and the molecular formula is C8H5F3O3, Related Products of catalysis-chemistry.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia