2,2-diphenylpropane-1,3-diol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 17.3 g. (0.076 mol.) of 2,2-diphenyl-1,3-propanediol in 200 ml. of dimethoxyethane is added 12.7 g. (0.3 mol.) of 57% sodium hydride followed by an additional 400 ml. of dimethoxyethane. After stirring overnight the suspension is cooled to 4° C. A solution of 31.2 g. (0.27 mol.) of sulfamoyl chloride in 600 ml. of dimethoxyethane is then added dropwise. The suspension is stirred overnight at room temperature. After filtering the mixture the filtrate is concentrated and the residue washed with heptane. Chromatography on SilicAR, CC-7, followed by crystallization affords 2,2-diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol. The suspension is stirred overnight at room temperature After filtering the mixture the filtrate is concentrated the residue washed with heptane Chromatography on SilicAR, CC-7, followed by crystallization

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

Procedure: 2,2-Diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol is prepared in an identical manner as the sulfamate reported in Example 1 except for the use of 2,2-diphenyl-1,3-propanediol (87.7 g., 0.385 mol.) as the alkanediol.

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

Procedure: 2,2-Diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol is prepared in an identical manner as the sulfamate reported in Example 1 except for the use of 2,2-diphenyl-1,3-propanediol (87.7 g., 0.385 mol.) as the alkanediol.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 17.3 g. (0.076 mol.) of 2,2-diphenyl-1,3-propanediol in 200 ml. of dimethoxyethane is added 12.7 g. (0.3 mol.) of 57% sodium hydride followed by an additional 400 ml. of dimethoxyethane. After stirring overnight the suspension is cooled to 4° C. A solution of 31.2 g. (0.27 mol.) of sulfamoyl chloride in 600 ml. of dimethoxyethane is then added dropwise. The suspension is stirred overnight at room temperature. After filtering the mixture the filtrate is concentrated and the residue washed with heptane. Chromatography on SilicAR, CC-7, followed by crystallization affords 2,2-diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol. The suspension is stirred overnight at room temperature After filtering the mixture the filtrate is concentrated the residue washed with heptane Chromatography on SilicAR, CC-7, followed by crystallization

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

Procedure: 42.5 g (0.2 M) of ethyl 2-oxo-2-(4-chlorophenyl)acetate are placed in 400 ml of CH2Cl2 in a 500 ml reactor. 22.8 g (0.1 M) of 2,2-diphenylpropane-1,3-diol and then 14.2 g (0.1 M) of BF3.Et2O are added. The mixture is left to react with stirring for 72 h at room temperature. The reaction mixture is taken up in NaHCO3 solution. The organic phase is washed with saturated NaCl solution. After drying over Na2SO4 and concentration, a very thick oil is obtained. 150 ml of isopropyl ether are added and a white precipitate forms. After filtration, 30 g of product melting at 156-158° C. are obtained (yield: 71%). The mixture is left to react The organic phase is washed with saturated NaCl solution After drying over Na2SO4 and concentration a very thick oil is obtained After filtration, 30 g of product melting at 156-158° C. are obtained (yield: 71%)

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

Procedure: A mixture of 22.8 g (0.1 M) of 2,2-diphenyl-1,3-propanediol and 100 g (0.98 M) of methyl pyruvate is brought to 70° C. in a 500 ml round-bottomed flask under a nitrogen atmosphere. 22.4 g (0.156 M) of P2O5 are added portionwise. An exothermic reaction takes place and the temperature rises to 98° C. The mixture is allowed to return to room temperature and is poured slowly into ice-cold water. This mixture is extracted with methylene chloride and the extracts are washed with sodium hydroxide and water. The extracts are concentrated and the residue is chromatographed by flash chromatography (70 CH2Cl2/50 cyclohexane eluent). The product is then recrystallized from 40 ml of diisopropyl ether. 7 g of a product of m.p. 116° C. are obtained. is brought to 70° C. in a 500 ml round-bottomed flask under a nitrogen atmosphere An exothermic reaction rises to 98° C to return to room temperature is poured slowly into ice-cold water This mixture is extracted with methylene chloride the extracts are washed with sodium hydroxide and water The extracts are concentrated the residue is chromatographed by flash chromatography (70 CH2Cl2/50 cyclohexane eluent) The product is then recrystallized from 40 ml of diisopropyl ether

Conditions: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 17.3 g. (0.076 mol.) of 2,2-diphenyl-1,3-propanediol in 200 ml. of dimethoxyethane is added 12.7 g. (0.3 mol.) of 57% sodium hydride followed by an additional 400 ml. of dimethoxyethane. After stirring overnight the suspension is cooled to 4° C. A solution of 31.2 g. (0.27 mol.) of sulfamoyl chloride in 600 ml. of dimethoxyethane is then added dropwise. The suspension is stirred overnight at room temperature. After filtering the mixture the filtrate is concentrated and the residue washed with heptane. Chromatography on SilicAR, CC-7, followed by crystallization affords 2,2-diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol. The suspension is stirred overnight at room temperature After filtering the mixture the filtrate is concentrated the residue washed with heptane Chromatography on SilicAR, CC-7, followed by crystallization

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

Procedure: 2,2-Diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol is prepared in an identical manner as the sulfamate reported in Example 1 except for the use of 2,2-diphenyl-1,3-propanediol (87.7 g., 0.385 mol.) as the alkanediol.