2- Acetyl-l-naphthol

The yield of 2-acetyl-l-naphthol, the in-cage product from 1-... 

Bismuth(III) triflate tetrahydrate can be utilized as a more commercially available catalyst for the Fries rearrangement of PAs to 2-hydrox-yaryl ketones. In the reaction with 1-naphthyl acetate, bismuth triflate (10% mol) gives the best yield in 2-acetyl-l-naphthol, the amount of... 

In the PFR of 1-naphthyl acetate, the yield of 2-acetyl-l-naphthol exhibits a positive external magnetic field effect for the ester labeled by the magnetically active isotope C, but no effect for the C ester. This effect is explained by considering hyperfine coupling between H or C of the naphthoxyl radical and the unpaired electron of the acetyl radical, which is in agreement with formation of the in-cage product from a singlet radical pair [42],... 

Acetyl-l-naphthol Oxime, in A-00026 a-Amino-l-naphthaleneacetic acid, A-00261... 

Acetyl-l-naphthol Ac, in A-00026 4-Hydroxy-3-biphenylcarboxylic acid Me ester, in H-00132... 

N-Acetyl analog. C13H 3N02, 4-acetamido-2-methyl-l-naphthol, K-Vitrat. Needles, mp 208-210s. Frepnt Veldstra, Wiardi, Rec. Trav. Chim. 62, 75 (1943),... 

Also obtained by reaction of fuming nitric acid with 4-acetyl-2-propionyl-l-naphthol in acetic acid [7767]. 

COCH2CH3 - Preparation by reaction of acetyl chloride with 2-propionyl-l-naphthol in the presence of zinc chloride in nitrobenzene (80%) [7767]. 

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-... 

It was first found that a chiral Yb catalyst, prepared in situ from Yb(OTf)3, (R)-(+)-l,T-bi-2-naphthol [(l )-BINOL], and a tertiary amine, in dichloromethane, was quite effective in enantioselective Diels-Alder reactions [36]. Some additives were also found to be effective not only in stabilizing the catalyst but also in controlling enantiofacial selectivity in the Diels-Alder reaction. When 3-acetyl-l,3-oxazolidin-2-one was combined with the chiral catalyst as an additive, the (2S,3R) form of the endo adduct was obtained in 93 % ee. When, on the other hand, 3-phenylacetylacetone was mixed with the catalyst as an additive, the (2R,3S) form of the endo adduct was obtained in 81 % ee [37]. 

The other part of the diaminonaphthol dihydrochloride solution is treated with acetic anhydride and then sodium acetate the reaction in aqueous solution effects selective acetylation of the amino groups and affords 2,4-diacetylamino-l-naphthol (4). Oxidation of 4 by Fe " and oxygen from the air is attended with cleavage of the acetylamino group at the 4-... 

R) -( + )-2-Acetyl-5,8-dimethoxy-l,2,3,4-tetrahydro-2-naphthol (173) is a key intermediate in the asymmetric synthesis of anthracycline antitumor agents demethoxyadriamycin (174 X = Y = OH) and 4-demethoxydaunomycin (174 X = Y = H) <94JOCli84>. The crucial step in a highly efficient asymmetric synthesis of (173) involves the enantioselective hydroxylation (>95% ee) of the potassium enolate of (171) with (—)-[(8,8-dimethoxycamphoryl)sulfonyl]-oxaziridine (158) to afford (172). Conversion to (173) was accomplished in three steps in 50% overall yield from (171) without racemization (Scheme 32). 

M)-Acetyl-5-acetylamino-l-methoxytryptamine (13) is of special interest because of its nature to change the reaction site depending on the nucleophile [33]. When 13 reacts with 2-naphthol in 85% HCOOH, Nb-acetyl-5-acetylamino-l-(2-hydroxynapht-l-yl)- (150,19%), Nb-acetyl-5-acetylamino-... 

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. 

Also obtained by boiling a 4-hydroxy-3-(l-oxopropyl)-l-naphthalenesulfonic acid and concentrated sulfuric acid mixture, followed by distillation [7757]. Also obtained by heating 4-propionyl-a-naphthol, 2,4-dipropionyl-a-naphthol or 4-acetyl-2-propionyl-a-naphthol with zinc chloride in acetic acid or propionic... 

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... 

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

Ac = Acetyl acac = Acetylacetonate bda = Benzylidene-acetone BINOL = l,l -bi-2-naphthol Bn = Benzyl brsm = Yield based on recovered starting material Bu = Bntyl CAN = Ceric anunonium nitrate CBS = Corey/Bakshi/Shibata catalyst [(+) or (—)-(S)-2-methyl-oxazaborolidine] COD = Cyclo-l,5-octadiene COT = Cyclooctatetraene Cp = Cyclopentadienyl Cp = Penta-methylcyclopentadienyl Cy = Cyclohexyl DCC = Dicy-clohexylcarbodiimde DMF = Ai,A-dimethylformainide DMPU = l,3-dunethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidin-one DMSO = Dimethylsnlfoxide dppe = Diphenylphosp-hinoethane dr = Diastereomer ratio dppm = Diphenylphos-phinomethane E = Electrophile ee = Enantiomeric excess EHMO = Extended htickel molecular orbital Et =... 

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