Butyl 2-formylphenyl

Butyl 2-Formylphenyl Tellurium5 A well-stirred mixture of 9.0 g (25 mmol) of butyl 2-(diethoxymethyl)-phenyl tellurium and 10 ml of concentrated hydrochloric acid is heated for 0.5 h. The solution is then cooled, extracted with diethyl ether, the extracts are dried with anhydrous magnesium sulfate, the solvent is evaporated, and the residue is distilled under reduced pressure yield 5.5 g (80%) b.p. 140-142°/0.1 torr. 

Blount and Robinson have extended this mode of synthesis to the preparation of iV-methyl/iomogranatonine (XXII) by the use of adipaldehyde, CHO. [CH2]4. CHO. The base, on reduetion with sodium in butyl aleohol, yields A -methyl/mmogranatoline (XXII CO — CHOH), the benzoyl derivative of which possesses marked local anaesthetic aetion. Similarly Blount, by eondensing /3-(o-formylphenyl)propaldehyde, CHO. CgH4. CHj. CHj. CHO, with methylamine and calcium acetonedicarboxylate, has prepared 8 9-benz-d - -feomogranatene-3-one (XXIII), which was reduced to the -alcohol (cf. reduction of tropinone to -tropine) and the latter converted to the benzoyl-derivative (m.p. 98°),... 

SchiflF bases of 2-formylphenyl butyl tellurium reacted with the stoichiometrically required amounts of thionyl chloride3, sulfuryl chloride4-5, bromine3-5 or iodine4-5 to produce the tellurium halides that are stabilized by coordination between the tellurium and nitrogen atoms. 

The Schiff base prepared from 2-formylphenyl butyl tellurium and 1,2-diaminoethane and a five-fold molar excess of bromine reacted to give the tellurium bromide3. With thionyl chloride the corresponding tellurium chloride (m.p. 246-248-1, from benzene) was obtained in 70% yield3. 

The Schiff base prepared from 2-formylphenyl butyl tellurium and 1,2-diaminoethane was converted to tellurium trihalides by excess sulfuryl chloride or bromine2. 

The oxidation of the formyl group in 2-formylphenyl butyl tellurium by silver oxide gave bis[2-curboxyphenyl] ditellurium in addition to the expected butyl 2-carboxyphenyl tellurium6. 

Alternatively, 2-formylphenyl butyl tellurium oxime can be cyclized in the presence of pyrophosphoric acid1. 

Benzotellurazole1 14.3 g (50 mmol) of 2-formylphenyl butyl tellurium, 3.8 g (55 mmol) of hydroxyl-amine hydrochloride, and 5.9 g (60 mmol) of fused potassium acetate are added to 100 ml of absolute ethanol and the mixture is heated under reflux with stirring for 2 h. The mixture is then concentrated, extracted with chloroform, and the extract is concentrated. The residue (the crude oxime) is added to a mixture of 50 ml of 85% phosphoric acid and 100 g of phosphorus pentoxide. This mixture is stirred and heated at 100° for 1 h, cooled, and poured into a mixture of ice and aqueous ammonia. The mixture is filtered, the solid is extracted with chloroform and the extract is dried and evaporated. The residue is recrystallized from methanol yield 4.6 g (40%) m.p. 173. ... 

The ease with which the Te — Te bond in ditellurium compounds is cleaved drastically limits the reactions for the modification of functional groups that are already present in the organic part of the molecules. The conversion of bis[2-carboxyphenyl] ditellurium to bis[chlorocarbonylphenyl] ditellurium by butyl dichloromethyl ether in the presence of anhydrous zinc chloride the acid hydrolysis of the ethylene acetals of bis[4-acetylphenyl] and bis[2-acetylphenyl] ditellurium to the bis[acetylphenyl] ditellurium derivatives, the saponification of bis[co-methoxycarbonylalkyl] ditelluriums to the corresponding bis[m-carboxyalkyl] ditelluriumand the oxidation of bis[2-formylphenyl] ditellurium by silver nitrate to bis[2-carboxyphenyl] ditellurium are the modifications of the organic moieties in diorgano ditellurium compounds that have been carried out successfully. 

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