1-Naphthol from tetralone

Tetralone from tetralone, alpha-naphthol, tetralin NaY Methyl acetate [241]... 

Several reports have suggested that carbo-carboxonium superelectrophiles may also be produced from phenols, naphthols, and related species, by diprotonation in superacidic media.34 For example, 1-naphthol is thought to form the distonic superelectrophile (93) with a variety of acids (excess AICI3, HF-SbFs, and HUSY zeolite).343 In the presence of benzene, the substituted tetralone, and with cyclohexane, 1-tetralone is produced (eq 34). 

Give the products resulting from the following reactions (a) 2-naphthol + MCN + ZnCI, + HCl (b) anthracene + cA-butene-dioic anhydride (c) nap ht ho-1.4-quin one + hcxa-2.4-dicne follow cd by reaction with CrO (d) naphthalene + phihalic anhydride -i-AlCl followed by reaction with polyphosphoric acid and then reduction and dehydlogenation (e) 1-tetralone + benzaldehyde + NaOH in ethanol. 

The reaction may also be performed over a mixed-oxide catalyst at 280° and 100 atm. of ethylene, which serves as the hydrogen acceptor, as illustrated by the preparation of /3-tetralone from 1,2,3,4-tetrahydro-2-naphthol. By the same procedure, diisobutyryl, a diketone, has been prepared from the acyloin (27%). ... 

Naphthols are reduced to P-tetralones (which are presumably protected from further reaction as the corresponding enolate anions) even more readily and it is surprising to find that even 6-methoxy-2-naph-thol (65) is converted into ketone (66 Scheme 11). ° Reduction of the equilenin ketal (67) was found to be highly dependent on the choice of metal. Reduction of (67 Scheme 12) or its sodium salt by lithium in the absence of an alcohol afforded (after acid hydrolysis) equilin (68) as the major product, whereas... 

The desire to avoid the demethylation of the 3-methoxy group in the preparation of estrogens by Schemes 35 and 36 made it necessary to study other possibilities for the synthesis of D-homoestrogens, starting from 6-hydroxy-l-tetralone (383) [458, 482-485] and its tetrahydropyranyl derivative [458, 463,475, 486] (Scheme 37). The initial 6-hydroxy-1-tetra-lone can be obtained either by demethylating the methoxy derivative (8) or by a four-stage synthesis from jS-naphthol with an over-all yield of about... 

Similar decomposition mechanisms have been found with other Pseudomonas strains (including P. multivorans) and with monomethyl and dimethyl naphthalenes, for example to methyl salicylic acids and to dimethyl salicylic acids (if both methyl groups were present in the same nucleus of the naphthalene), or to methyl naphthalene carboxylic acids [51]. On the other hand, Cunninghamella el-egans metabolizes naphthalene to trans-l,2-dihydrodiol, from which 1-naphthol, 1,4-naphthoquinone and 4-hydroxy-1-tetralone are formed as intermediates for further decomposition [126, 127]. 

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