Benzaldehyde, 2,3-dimethoxy 2-methyl

Ethanone, 1- [3-(l,l-dimethylethyl)-4-methoxy-5-nitrophenyl Benzaldehyde, 2 (l,l-dimethylethyl)-4-methoxy-5-nitro Benzene, 1,4-BIS- (1, l-dimethylethyl)-2 methoxy-5-nitro Benzene, 1-(1, l-dimethylethyl)-2, 5-dimethoxy-4-nitro Benzene, 1-(1, l-dimethylethyl)-2-methoxy-4 methyl-5-nitro Benzaldehyde, 5- (1, l-dimethylethyl)-2-methyl-3-nitro Benzaldehyde, 2- (1, l-dimethylethyl)-4,5,6-trimethyl-3-nitro Benzene, 5-(l, l-dimethylethyl)-2-methoxy-l, 3-dinitro Benzene, 1-(1, l-dimethylethyl)-4-methoxy-2-methyl 3-5-dinitro Benzene, 2-bromo-5- (1, l-dimethylethyl)-4-methoxy-l,... 

The last of the butyl isomers, the tert-butyl compound, was made from a much more obvious starting material. This is the commercially available tert-butyl hydroquinone. It was methylated in sodium hydroxide with methyl iodide, and then carried through the above sequence (benzaldehyde. mp 124 °C from cyclohexane, nitrostyrene, yellow crystals from methanol, mp 95-96.5 °C, and lithium aluminum hydride reduction) to give 2,5-dimethoxy-4-(l,l-dimethylethyl)amphetamine hydrochloride (DOTB, mp 168 °C). Rats trained in a process called the Sidman Avoidance Schedule gave behavior that suggested that DOTB had no activity at all, and in human trials, doses of up to 25 milligrams were totally without effect. 

D Auria and coworkers investigated the photocycloaddition of 5-methyl-2-furyl-phenylmethanol 92 with benzophenone resulting in two adducts 93 and 94 in a 1 1 ratio while the addition to 4,4/-dimethoxy-benzophenone, benzaldehyde or 4-methoxybenzaldehyde, respectively, gave merely the adducts 93 (Sch. 27) [88]. 

Proof of the structure [xi] was sought and found by the oxidation of phenyldihydrothebaine with alkaline potassium permanganate, which resulted in the production of benzaldehyde, benzoic acid, and 4-methoxyphthalic acid. By exhaustive methylation of the methyl ether the optically active (+)-3 4-dimethoxy-2-(5-methoxy-2-vinylphenyl) stilbene [xn] (prepared by Freund [1], but stated to be optically inactive) was obtained, and permanganate oxidation of this afforded 5 6 5 -trimethoxydiphenaldehyde [xm] (also obtained by the ozonoly-sis of [xn]) and 5 6 5 -trimethoxydiphenic acid [xrv] (also obtained by oxidation of [xm]). This acid was identified with an authentic specimen prepared in stages from 4-acetoxy-3 6-dimethoxyphenanthrene quinone (acetylthebaolquinone [xv]) [6-7, 9-10],... 

According to one Indian manufacturer 3,5-dimethoxy p-cresol is initially oxidized to 3,5-dimethoxy-4-hydroxy-benzaldehyde (syringe aldehyde) which is then methylated to 3,4,5-TMBA... 

Recently, Nakamura et al. successfully synthesized a regioisomer of kealiiquinone (Scheme 11) [50]. l-Methyl-2-phenylthio-lff-imidazole 44 was first converted into the 5-substituted imidazole 45, then the benzylic hydroxyl group in 45 was protected by a ferf-butyldimethylsilyl (TBDMS) group, and bromination with N-bromosuccinimide gave the bromide 46. Lithiation by ferf-butyllithium at the 4-position of 46 followed by trapping with 3,4-dimethoxy-2-(methoxymethoxy)benzaldehyde gave the tetrasubstituted imidazole 47 as a diastereomeric mixture. Acetylation of the hydroxy group of 47... 

Die Reduktion von 4-Hydroxy-3-methoxy-benzaldehyd (Vanillin) mit Kalium/fl. Ammoniak bei 20° fiihrt zu 2 -Methoxy-4-hydroxymethyl-phenol und dem Kondensationspro-dukt 3,4 -Dihydroxy-3, 4-dimethoxy 6-methyl-benzophenon (F 232°)s ... 

A sigruficant use is as a catalyst in a multitude of reactions, such as the formation of acrjdic and methacrjdic acid amides from fatty acid amides (81) of cychc ketones such as 4-phen5icyclopentane-l,2-dione and 2,5-dihydroxy-/)-benzoquinone from benzaldehyde diethji acetal and 2,4-dioxo-5,5-dimethoxy-hexanoic acid methyl ester (82) of dimer aldehydes from propane (83) and for the polymerization of epoxy compounds (84). Mag nesium Kthylate. Magnesium ethoxide [2414-98-4]y Mg(OC2H 2 niol wt 114.4, is an almost white hygroscopic powder density,... 

Most of the reactions of laudanosine have been carried out with the racemic mixture obtainable by reduction of quaternary papaverinium salts (p. 36). For instance, Gadamer and Kondo (79) obtained by oxidation with mercuric acetate, veratraldehyde and 4,5-dimethoxy-2-( 3-methyl-aminoethyl) benzaldehyde (XLVI) (or its ring-chain tautomer, laudaline), which resembles cotarnine in its properties. The same products are formed when manganese dioxide is chosen as the oxidizing agent (80). In both... 

Dimethoxy-2- 3-dimethylaminoethyl)henzaldehyde (IV).—This base yielded an oxime and seemed to be the methyl derivative of 4,5-dimethoxy-2-(/3-methylaminoethyl)benzaldehyde, which Pyman (23) had obtained... 

ARIADNE itself, reduced not with LAH or AH (which would give the primary amine), but rather with sodium borohydride and borane dimethylsulfide. The product, 1-(2,5-dimethoxy-4-methylphenyl)-N-hydroxy-2-aminobutane hydrochloride, was a white crystalline material. The TOM analogue got as far as the nitrostyrene. This was made from 2-methoxy-4-methyl-5-(methylthio)benzaldehyde (see under the 5-TOM recipe for its preparation) and nitropropane in acetic acid, and gave bright yellow crystals. The true pseudo-analogue is the 2,4,6-trimethoxy material based on TMA-6, which is the "real" pseudo-TMA-2. The nitrostyrene from 2,4,6-trimethoxybenzaldehyde and nitropropane crystallized from MeOH/CH3CN as fine yellow crystals, and this was reduced with AH in cold THF to 1-(2,4,6-trimethoxyphenyl)-2-aminobutane which was a bright, white powder. 

A mixture of 72 g POCI3 and 67 g N-methylformanilide was heated for 10 min on the steam bath. To this claret-colored solution was added 28 g of 2,5-dimethoxyphenyl (t)-butyl sulfide, and the mixture heated for 10 min on the steam bath. This was then added to 1 L of H20 and stirred overnight. The residual brown oil was separated from the water mechanically, and treated with 150 mL boiling hexane. The hexane solution was decanted from some insoluble tars, and on cooling deposited a dark oil which did not crystallize. The remaining hexane was removed under vacuum and the residue combined with the above hexane-insoluble dark oil, and all distilled at 0.2 mm/Hg. An early fraction (70-110 °C) was largely N-methyl-formanilide and was discarded. Crude 2,5-dimethoxy-4-(t-butylthio)benzaldehyde came over at 120-130 °C... 

A suspension of 12.5 g of crude 5-formyl-7-methoxy-2-oxo-1,3-benzoxathiole in 100 mL MeOH containing 28.4 g methyl iodide was treated with a solution of 12 g NaOH in 100 mL warm MeOH. The mixture was held at reflux for 1 h and then the solvents were removed under vacuum. A solution of 14.2 g methyl iodide in 100 mL DMSO was added and the mixture stirred for 1 h. An additional 2.4 g of NaOH and 16 g methyl iodide were added, and the stirring was continued for another 2 h. The reaction mixture was poured into 800 mL H20, acidified with HCI, and extracted with 3x75 mL CH2CI2. The pooled extracts were washed with 5% NaOH, then water, and the solvent removed under vacuum. Distillation at 110-130 °C at 0.4 mm/Hg gave 0.9 g 3,4-dimethoxy-5-(methylthio)benzaldehyde which had a mp of 57-58 °C after crystallization from EtOH. Anal. (C10H12O3S) C,H. 

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