Trivial names phenols

Tablel.10 Retained Trivial Names of Alcohols and Phenols with Structures 1.24...

For monosubstituted alkylphenols, the position of the alkyl radical relative to the hydroxyl function is designated either with a numerical locant or ortho, meta, or para. The alkyl side chain typically retains a trivial name. Thus 4-(l,l,3,3-tetramethylbutyl)phenol, 4-/ f2 octylphenol, and para-tert-octy Tph.eno (PTOP) all refer to stmcture (1). 

Diazotization of 3,7-diaminodibenzothiophene 5,5-dioxide, which has the trivial name of benzidine sulfone, followed by coupling with phenols, anilines, or arylsulfonic acids gives bis-azo dyes varying in color from red-brown to blue. These dyes are useful for the coloring of plastics and cellulose. second class of compounds based on 3,7-diamino-... 

Salicin is an (9-glycoside of a phenol, namely salicyl alcohol. Salicin is a natural antipyretic and analgesic found in willow bark, and is the template from which aspirin (acetylsalicylic acid, see Box 7.13) was developed. Prunasin from cherry laurel is an example of a cyanogenic glycoside, hydrolysis of which leads to release of toxic HCN (see Box 7.7). It is the (9-glucoside of the alcohol mandelonitrile, the trivial name for the cyanohydrin of benzaldehyde. It is the further hydrolysis of mandelonitrile that liberates HCN. 

Benzene derivatives are named by prefixing the name of the substituent group to the word benzene, e.g. chlorobenzene and nitrobenzene. Many benzene derivatives have trivial names, which may show no resemblance to the name of the attached substituent group, e.g. phenol, toluene and aniline. 

The C-2 and C-3 hydroxy derivatives of pyrrole are special in the sense that the tautomeric equilibria favor the pyrrolinone structures (see Section 3.04.6.2). Furthermore, the general synthetic methods are not usually applicable so that we will call attention in this section not only to the methods of directly introducing these substituents, which are rare, but also to those ring construction processes which specifically give the pyrrolinones and indolinones. The indole derivatives have widely used trivial names, oxindole (5) for indolin-2-one and indoxyl (6) for indolin-3-one, Carbocyclic hydroxy substituents in indole and carbazole, on the other hand, for the most part act as normal aromatic phenolic groups. These compounds are usually prepared by application of the standard ring syntheses. 

Many trivial names persist, particularly for aromatic, or arene alcohols (phenols) ... 

An organoleptic omission test on this mixture confirmed 3-hydroxy-4, 5-dimethyl-2(5H)-furanone to be the most important FIC for a raw cane sugar aroma, and the other main components in Table 1, i.e., vanillin, maltol, 4-pentyl butanolide, 4-vinyl phenol and 2,6-dimethoxy phenol, seemed to improve the overall sugary aroma. From these results, we( ) gave the trivial name sotolon" to 2-hydroxy-4,5-dimethyl-2(5H)-furanone, which is built up from "soto" (raw sugar in Japanese) and "olon" (enol lactone) as a main FIC in raw cane sugar. 

The dihydroxybenzenes or dihydric phenols 15-17 have trivial names as shown. 

Not surprisingly, three nitro groups have an even greater influence on the reactivity of the halogen and 1-chloro-2,4,6-trinitrobenzene (picryl chloride) is hydrolysed to 2,4,6-trinitrophenol (picric acid) in boiling water. The trivial names tell us that this aryl halide behaves as an acyl halide and the phenol as an acid. 

The principle of giving the lowest locants to the simplest or what is considered the most important modifications has often been applied to trivial names. Whenever the starting point is unambiguous as in toluene, phenol, or benzoic acid, where the ring atom connected with the modification is numbered 1, the success is satisfactory. However, the confusion possible with trivial names containing several substituents is familiar from the cresols and toluidines. There is no reason why an agreement between these numbering principles should not be reached. 

The three monohydroxy derivatives of phenol are all well-known componnds, the o-, m- and p-species with the long-established, trivial names catechol, resorcinol and hydro-quinone. These compounds are all benzenediols and, as snch, they and their snbstimted derivatives will be discussed later in this text. 

It has been proposed that the dihydrothebaine formed hy sodium reduction of thebaine (so-called phenolic dihydrothebaine) be renamed dihydrothebaine-

trivial name for an older one does not appear legitimate once a structure is established beyond doubt. We would prefer the term A < >-dehydrothebainol methyl ether for the sodium-ethanol or sodium-ammonia reduction product (CCCLIV), The lithium aluminum hydride reduction product would then be A h4).(jeijy(ji.o< hel3ajnol methyl ether (CCCLV), and the third isomer, obtained by base-catalyzed rearrangement of codeine methyl ether, would be A -dehydrothebainol methyl ether (CCCLVI). 

Compounds are mentioned by their trivial names and respective codes of the Dictionary of Natural Products [2] are given in parentheses. When no trivial names were coined, only the codes are given. The bonds which may have been formed by oxidative phenolic coupling are indicated by heavy lines. 

Each of the following phenol or quinone derivatives has the common or trivial name shown and is a compound of some significance. Provide the lUPAC name and synthesize each from the starting material given. 

Unfortunately, many natural coumarins have been assigned trivial names, mostly botanically derived. Although these can facilitate discussion, to a considerable extent they serve to confuse, especially since many of the endings (e,g, -ol, -one) are not at all consistent with structure. Thus umbelliferone (2) is a phenol while osthol (143) is the methyl ether of osthenol (142). Structurally closely related coumarins can have markedly different names aculeatin (249) is the epoxide of toddaculin (248), both of which occur in Toddalia aculeata, while conversely almost identical trivial names can be given to structurally quite dissimilar coumarins, e. g. ferudenol (339) and ferulenol (481). Not infrequently, the same coumarin isolated by different workers from different plant sources is given two or even three trivial names and even enantiomers are known with distinct trivial names, e.g. marmesin (103) and nodakenetin (104). 

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