The Hydrogenation of Phenolic Acids

Abstract

Ungnade and F. V. Morriss Yol. 70 time. New procedures for preparing o-fluorostyrene, o-methoxystyrene and o-cyanostyrene are described.Two more examples of the disproportionation of phenylmethylcarbinols to ethylbenzenes under the influence of activated alumina have been observed in the dehydration of p-benzylphenylmethylcarbinol and o-methoxyphenylmethylcarbinol. Urbana, Illinois

Potential Reserpine Analogues: Part III Derivatives of 4-ethoxycarbonyloxy-3,5-dimethoxy-benzoic acid, 3-dimethylaminobenzoic acid, p-hydroxybenzanilide and N-(3,4-dimethoxyphenethyl)-3(or 4)-hydroxycyclohexane carboxyamide

“…Method (6). Ethyl 3-hydroxycyelohexanecarboxylate (as prepared by Ungnade and Morriss, 1948) (1.14 g.) and homoveratrylamine (1.15 g.) were similarly treated for 3 hr. and the reaction product was recrystallised four times from benzene to yield the crystalline amide, m.p.…”

Generating rapamycin analogues by directed biosynthesis: starter acid substrate specificity of mono-substituted cyclohexane carboxylic acids

“…This represents a significant (3.5 fold) improvement on the analogous reported yield of only 6.7% for the fluorination of a 4-hydroxycyclohexane carboxylate derivitive. 16 In conclusion we describe a considerably improved synthesis of 4-fluorocyclohexane carboxylic acid (12), with a 3.5 fold improvement in the fluorination step. The administration of both 4-and 3-hydroxycyclohexane carboxylic acid and 3-hydroxycyclohex-1ene carboxylic acid to S. hygroscopicus (MG2-10) lead to the production of pre-rapamycin analogues whereas 2-hydroxy, 4-fluoroand 4,4-difluorocyclohexane carboxylic acid does not.…”

“…4-, 3-And 2-hydroxycyclohexane carboxylic acids 5, 6 and 7 were generated as a mixture of cis and trans isomers through catalytic hydrogenation of their corresponding hydroxybenzoate ethyl esters, 12 followed by base catalysed hydrolysis. The resultant hydroxylated cyclohexane carboxylic acids were administered at a final concentration of 2 mM, as previously described 11 to cultures of S. hygroscopicus (MG2-10) and the production of prerapamycin analogues analysed by LC-MS (Table 1).…”

“…4-Fluorocyclohexanoic acid 12 and a commercial sample of 4,4-difluorocyclohexanoic acid 13 ‡ were administered to the test organism described above. No pre-rapamycins were generated indicating the necessity for hydroxylation of the ring of the starter acid prior to its incorporation and showing that fluorination precluded further enzymatic oxidation of the substrates in vivo.In conclusion we describe a considerably improved synthesis of 4-fluorocyclohexane carboxylic acid(12), with a 3.5 fold improvement in the fluorination step. The administration of both 4-and 3-hydroxycyclohexane carboxylic acid and 3-hydroxycyclohex-1ene carboxylic acid to S. hygroscopicus (MG2-10) lead to the production of pre-rapamycin analogues whereas 2-hydroxy, 4-fluoroand 4,4-difluorocyclohexane carboxylic acid does not.…”

Synthesis of trans‐4‐(ω‐Cyanalkyl)‐cyclohexanols

“…Die Arbeitsvorschriften werden jeweils am reprgsentativen Beispiel von Derivet c (n = 2) erlgutert. 0,9 KPa [16] Nach Chromatographie mit Ether/Hexan (2: 1) kristdlisiert dss Produkt. in Iangen Stlbehen (Fp.…”