1,1'-ethane-1,1-diyldibenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: They can be prepared by a variety of chemical synthetic manners, and for example, phenyl-(vinylpheny)ethane may be prepared by reacting diphenylethane with acetyl chloride in the presence of a Friedel-Crafts catalyst to form phenyl(acetylphenyl)ethane, reducing the latter with sodium boron hydrine or the like, and dehydrating it. Phenyl(isopropenylphenyl)ethane can be prepared by reacting phenyl(formylphenyl)ethane with a Grignard reagent such as methylmagnesium iodide, and carrying out dehydration. They can be prepared by a variety of chemical synthetic manners

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3(a) An aromatic polyamine mixture made up of 2.6% of diaminotoluene (isomer mixture), 6.2% of diaminomethyl diphenylmethane (isomer mixture containing more than 90% of diamines of the type containing one amino substituent on each aromatic ring) and 91.2% of triamino-methyl diphenyl methane (isomer mixture containing more than 90% of triamines with one amino group on the unsubstituted aromatic ring and two amino groups on the methyl-substitued aromatic ring) was obtained by the nitration of methyl diphenyl methane, followed by catalytic hydrogenation using Raney nickel in accordance with European Patent Application No. 46,917. 350 g of this polyamine mixture were hydrogenated at 200° C./275 bars in accordance with Example 1(a) in the presence of 35 g of ruthenium (5%)/aluminum oxide supported catalyst and 35 g of ammonia in a 0.7 liter stirrer-equipped autoclave. After distillation twice, the hydrogenation product which was 91% triaminomethyl dicyclohexyl methane corresponding to formula (I) (R=CH3), and 9% diaminomethyl dicyclohexyl methane, was isolated in a yield of 69.2 g (B.p. 132°-148° C./0.1 mbar).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: For example, vinylnaphthalene may be obtained by reacting formylnaphthalene with a Grignard reagent such as methyl magnesium iodide and then dehydrating the reaction product. Vinylphenylphenylethane may be obtained by reacting diphenylethane with acetyl chloride in the presence of a Friedel-Craft catalyst to produce acetylphenylphenylethane, reducing the thus produced product with sodium boron hydride and then dehydrating the thus reduced product. Isopropenylphenylphenylethane may be obtained by reacting formylphenylphenylethane with a Grignard reagent such as methyl magnesium iodide and then dehydrating the reaction product. 1,2-diphenylethylene may be obtained by reacting benzaldehyde with benzyl magnesium bromide and then dehydrating the reaction product; 1,2-diphenylpropene may likewise be obtained.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: For example, vinylnaphthalene may be obtained by reacting formylnaphthalene with a Grignard reagent such as methyl magnesium iodide and then dehydrating the reaction product. Vinylphenylphenylethane may be obtained by reacting diphenylethane with acetyl chloride in the presence of a Friedel-Craft catalyst to produce acetylphenylphenylethane, reducing the thus produced product with sodium boron hydride and then dehydrating the thus reduced product. Isopropenylphenylphenylethane may be obtained by reacting formylphenylphenylethane with a Grignard reagent such as methyl magnesium iodide and then dehydrating the reaction product. 1,2-diphenylethylene may be obtained by reacting benzaldehyde with benzyl magnesium bromide and then dehydrating the reaction product; 1,2-diphenylpropene may likewise be obtained.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: For instance, vinylnaphthalene is prepared by reacting formylnaphthalene with a Grignard reagent such as methylmagnesium iodide, and then dehydrating. Phenyl(vinylphenyl)ethane is prepared by reacting diphenylethane with acetyl chloride in the presence of a Friedel-Crafts catalyst to obtain phenyl(acetylphenyl)ethane, reducing by sodium borohydride, and then dehydrating. Phenyl(isopropenylphenyl)ethane is prepared by reacting phenyl(acetylphenyl)ethane with a Grignard reagent such as methylmagnesium iodide, and then dehydrating. 1,2-Diphenylethylene is prepared by reacting benzaldehyde with benzylmagnesium bromide, and then dehydrating. 1,2-Diphenylpropene is also prepared by a similar method. 1,1-Diphenylethylene is prepared by reacting diphenyl ketone with a Grignard reagent such as methylmagnesium iodide, and then dehydrating.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: When styrene is reacted with, for example, benzene, toluene or xylene according to the method of the present invention, 1,1-diaryl-ethane such as 1,1-diphenyl-ethane, 1-phenyl-1-tolyl-ethane, or 1-phenyl-1-xylyl-ethane is obtained, respectively, as an aralkylation product.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: These compounds can be prepared through various chemical synthesis methods. For example, phenyl(vinylphenyl)ethane is prepared by reacting diphenylethane with acetyl chloride in the presence of Friedel-Crafts catalyst to obtain phenyl(acetylphenyl)ethane, then it is reduced with sodium borohydride and dehydrated. Phenyl(isopropenylphenyl)ethane is prepared by reacting phenyl(formylpheny)ethane with a Grignard reagent such as methylmagnesium iodide, which is followed by dehydration. These compounds can be prepared through various chemical synthesis methods

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: They can be prepared by a variety of chemical synthetic manners, and for example, phenyl-(vinylpheny)ethane may be prepared by reacting diphenylethane with acetyl chloride in the presence of a Friedel-Crafts catalyst to form phenyl(acetylphenyl)ethane, reducing the latter with sodium boron hydrine or the like, and dehydrating it. Phenyl(isopropenylphenyl)ethane can be prepared by reacting phenyl(formylphenyl)ethane with a Grignard reagent such as methylmagnesium iodide, and carrying out dehydration. They can be prepared by a variety of chemical synthetic manners

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3(a) An aromatic polyamine mixture made up of 2.6% of diaminotoluene (isomer mixture), 6.2% of diaminomethyl diphenylmethane (isomer mixture containing more than 90% of diamines of the type containing one amino substituent on each aromatic ring) and 91.2% of triamino-methyl diphenyl methane (isomer mixture containing more than 90% of triamines with one amino group on the unsubstituted aromatic ring and two amino groups on the methyl-substitued aromatic ring) was obtained by the nitration of methyl diphenyl methane, followed by catalytic hydrogenation using Raney nickel in accordance with European Patent Application No. 46,917. 350 g of this polyamine mixture were hydrogenated at 200° C./275 bars in accordance with Example 1(a) in the presence of 35 g of ruthenium (5%)/aluminum oxide supported catalyst and 35 g of ammonia in a 0.7 liter stirrer-equipped autoclave. After distillation twice, the hydrogenation product which was 91% triaminomethyl dicyclohexyl methane corresponding to formula (I) (R=CH3), and 9% diaminomethyl dicyclohexyl methane, was isolated in a yield of 69.2 g (B.p. 132°-148° C./0.1 mbar).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: For instance, vinylnaphthalene is prepared by reacting formylnaphthalene with a Grignard reagent such as methylmagnesium iodide, and then dehydrating. Phenyl(vinylphenyl)ethane is prepared by reacting diphenylethane with acetyl chloride in the presence of a Friedel-Crafts catalyst to obtain phenyl(acetylphenyl)ethane, reducing by sodium borohydride, and then dehydrating. Phenyl(isopropenylphenyl)ethane is prepared by reacting phenyl(formylphenyl)ethane with a Grignard reagent such as methylmagnesium iodide, and then dehydrating. 1,2-Diphenylethylene is prepared by reacting benzaldehyde with benzylmagnesium bromide, and then dehydrating. 1,2-Diphenylpropene is also prepared by a similar method. 1,1-Diphenylethylene is prepared by reacting diphenyl ketone with a Grignard reagent such as methylmagnesium iodide, and then dehydrating.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: For instance, vinylnaphthalene is prepared by reacting formylnaphthalene with a Grignard reagent such as methylmagnesium iodide, and then dehydrating. Phenyl(vinylphenyl)ethane is prepared by reacting diphenylethane with acetyl chloride in the presence of a Friedel-Crafts catalyst to obtain phenyl(acetylphenyl)ethane, reducing by sodium borohydride, and then dehydrating. Phenyl(isopropenylphenyl)ethane is prepared by reacting phenyl(formylphenyl)ethane with a Grignard reagent such as methylmagnesium iodide, and then dehydrating. 1,2-Diphenylethylene is prepared by reacting benzaldehyde with benzylmagnesium bromide, and then dehydrating. 1,2-Diphenylpropene is also prepared by a similar method. 1,1-Diphenylethylene is prepared by reacting diphenyl ketone with a Grignard reagent such as methylmagnesium iodide, and then dehydrating.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: One known synthesis of this odorant is based on the Friedel-Crafts reaction of styrene with benzene (see Spilker and Schade, Chem. Berichte, 65 (1932), 1686. The product 1,1-diphenylethane was obtained in only 25% yield. Other procedures described in the literature, for example the reaction of benzyl chloride with toluene and cupric chlorides as catalysts (U.S. Pat. No. 3,679,760) or the oxidative coupling of ethylbenzene and benzene with a catalyst consisting of aluminum and cupric chlorides (U.S. Pat. No. 3,631,211) produce only low yields and/or require costly starting materials, so that industrial use is not practical. synthesis of this odorant