1- Acetyl-2-naphthol

Metho naphthaldehyd l) 8II174. 3>Metho 4>ozo-l -methylen-l. 4-dihydro haphthalin 8 1 565. l Metbozy Daphthaldehyd (2) 8,148. l Aoetyl naphthol (2) 81566, II174. 4>Acetyl-naphthol (l) 8 1 566, II176. 2-Acetyl-naphthol-(l) 8,149,1567, II178. 3 Acetyl-naphthol- (l) 8,150. 3 Acetyl-naphthoh(2) 81 179. 

The procedure is not usually applicable to aminosulphonic acids owing to the interaction between the amino group and the phosphorus pentachloride. If, however, the chlorosulphonic acid is prepared by diazotisation and treatment with a solution of cuprous chloride in hydrochloric acid, the crystalline chlorosulphonamide and chlorosulphonanilide may be obtained in the usual way. With some compounds, the amino group may be protected by acetylation. Sulphonic acids derived from a phenol or naphthol cannot be converted into the sulphonyl chlorides by the phosphorus pentachloride method. 

This method has been used for the preparation of other phenolic ketones such as resacetophenone, 2-acetyl-i-naphthol,i 2-phenylacetyl-i-naphthol and 2-phenylpropionyl-i-naphthol. ... 

Sen and Kakaji synthesized a series of 4-butyrylnaphthocoumarins 48 from l-butyryl-2-naphthols 49 using acetic anhydride and two homolog anhydrides in excellent yields. They also showed that l-propionyl-2-naphthols and l-acetyl-2-naphthols could be converted to their corresponding coumarins using the same three anhydrides. However, l-acetyl-2-naphthol in the presence of acetic anhydride and sodium acetate gave a chromone not a coumarin. 

Benzoxepins are capable of rearranging to naphthalene derivatives 4 and 5 under thermal conditions.182,185,246,247 When 3,5-diacetoxy-4-phenyl-l-benzoxepinis heated to 150°C a mixture of 1- and 2-naphthol derivatives 4a and 5a is obtained due to the intramolecular acetylation of the reactive intermediate.246... 

Typical preparation of naphthopyran 32 involves Fries rearrangement of 1-acetoxynaphthalene 30. Condensation of 2-acetyl- 1-naphthol 31 with adamantanone, followed by usual reduction and dehydration gives 32 (Scheme 16).70... 

A chiral hydride complex, tentatively assumed to be 86, prepared by partially reacting LAH with (- )-N-methylephedrine (1 equivalent) and /V-ethylaniline (2 equivalents) was found to reduce 2-acetyl-5,8-dimethoxy-3,4-dihydronaphtha-lene (87) quantitatively to the (- )-carbinol (88) with 92% e.e. (94,95). Carbinol 88, which was obtained optically pure by recrystallization, could be converted to (/ )-(-)-2-acetyl-5,8-dimethoxy-l,2,3,4-tetrahydro-2-naphthol (89). The lat-... 

The esters of naphthol have also been reported to undergo photochemical rearrangement. 1-Naphthyl acetate (60) [28,39,50] gives 2- and 4-acetyl-1-naph-... 

C12H11JNO2 l-Acetyl-2-naphthol oxime Determination Gravimetric Cu Mn, Ni, Pd 3... 

Synthesis of racemic naproxene Friedel-Crafts acylation (aluminum chloride - nitrobenzene) of p-naphthol methyl ether affords 2-acetyl-6-methoxy naphthalene, which, when treated with either dimethyl sulfonium or dimethylsulfoxonium methylide, gives 2-(6-methoxynaphthalen-2-yl)propylene oxide. Treatment of the latter with boron trifluoride etherate in tetrahydrofuran gives 2-(6-methoxynaphthalen-2-yl)propionaldehyde, which is oxidized using Jones reagent (4 M chromic acid) to yield the racemic 2-(6-methoxynaphthalen-2-yl)propionic acid. 

Satchell87 found that the acylation, in nitromethane, of 0-naphthol by acetyl chloride to be catalysed by hydrogen chloride, and that added chloride ions depress the rate by a mass law effect. Both unionised and ionised acetyl chloride take part in the acylation and although the ionisation is kinetically independent of the amount of hydrogen chloride, the observed increase in rate by added hydrogen chloride can be explained most easily on the basis that the ionisation is dependent on the presence of HC1, the mechanism being... 

Contribution to the overall rate from steps 1 and 3 are approximately equal, and that from 2 is thought to be quite small and although an alternative mechanism such as via (CH3COClH)+ which fits the kinetics may be possible, and indeed may be present, it is probably not as prominent as that via CH3CO+HCl2". Satchell107 found that the reaction of acetyl chloride with 0-naphthol was... 

Although in the reaction of acetyl chloride with 0-naphthol (in nitromethane) unionised halide was thought to be implicated, Satchell108 has shown that in the case of acetyl bromide (in acetonitrile) there is strong evidence that reaction proceeds via free and ion-paired acetylium ions, viz. 

The reactions of 0-naphthol and 4-methoxyphenol with acetyl, propionyl, butyryl, 0-chloropropionyl and chloracetyl chlorides in acetonitrile produce some striking kinetic results109. The behaviour of acetyl, propionyl and n-butyryl chlorides fit reasonably well into the pattern for acetyl chloride in nitromethane and acetyl bromide in acetonitrile. However, with chloracetyl chloride the mechanism is essentially a synchronous displacement of covalently bound chlorine by the phenol and this process is powerfully catalysed by added salt with bond breaking being kinetically dominant. When no added salt is present the rate of hydrolysis of chloracetyl chloride is ca. 8000 times slower than that of acetyl chloride. Although, normally, in second-order acylation reactions, substituents with the greatest electron demand have been found to have the fastest rates, the reverse is true in this system. Satchell proposes that a route such as... 

Phenols and naphthols also can be readily acetylated, using acetic anhydride. The general method is shown in the next preparation. 

Palatine scarlet, xylidine ponceau. Victoria scarlet, lanafuchswe, sorbine red. Biebnch acid red. crystal scarlet fast red. croeaine scarlet, Biebnch scarlet, wool and cloth h reds, wool scarlet, acetyl red, amido naphthol red, enocarmme, enorubine, azo acid ° red. Guinea fast red, fast acid cochineal, etc S o to ff 8. Decolorised 1 Colour is not restored either by air or by persulphate Axo Class Boil with dihitc bichromate Ks j f If 18 p P srs >< 1 s > j-... 

An important coupling component for paper dyes is 2-amino-5-naphthol-7-sulfonic acid (12) and its derivatives (R= H, acetyl, benzoyl, aryl, imidazoyl, thi-azolyl, triazolyl, etc.). 

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