methyl tridecanoate

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

Procedure: A solution of tridecanoic acid, methyl ester (24.63 g, 0.1078 mol), and anhydrous hydrazine (3.40 mL, 0.108 mol) in absolute ethanol (150 mL) was stirred at room temperature for 24 hours, then refluxed 2 days. The solution was allowed to cool, and the solid that crystallized was filtered off, washed, and dried in vacuo; yield 18.6 g (75%); mp 101°-104° C. refluxed 2 days to cool the solid that crystallized was filtered off washed dried in vacuo

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

Procedure: A solution of tridecanoic acid, methyl ester (24.63 g, 0.1078 mol), and anhydrous hydrazine (3.40 mL, 0.108 mol) in absolute ethanol (150 mL) was stirred at room temperature for 24 hours, then refluxed 2 days. The solution was allowed to cool, and the solid that crystallized was filtered off, washed, and dried in vacuo; yield 18.6 g (75%); mp 101°-104° C. refluxed 2 days to cool the solid that crystallized was filtered off washed dried in vacuo

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

Procedure: A solution of tridecanoic acid, methyl ester (24.63 g, 0.1078 mol), and anhydrous hydrazine (3.40 mL, 0.108 mol) in absolute ethanol (150 mL) was stirred at room temperature for 24 hours, then refluxed 2 days. The solution was allowed to cool, and the solid that crystallized was filtered off, washed, and dried in vacuo; yield 18.6 g (75%); mp 101°-104° C. refluxed 2 days to cool the solid that crystallized was filtered off washed dried in vacuo

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

Procedure: A solution of tridecanoic acid, methyl ester (24.63 g, 0.1078 mol), and anhydrous hydrazine (3.40 mL, 0.108 mol) in absolute ethanol (150 mL) was stirred at room temperature for 24 hours, then refluxed 2 days. The solution was allowed to cool, and the solid that crystallized was filtered off, washed, and dried in vacuo; yield 18.6 g (75%); mp 101°-104° C. refluxed 2 days to cool the solid that crystallized was filtered off washed dried in vacuo

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

Procedure: A mixture of methyl tridecanoate isomers, 95% pure and containing 65% methyl n-tridecanoate, was subjected to partial hydrolysis under basic conditions. A 10 ml amount of the isomer mixture was placed with 10 ml water in a flask equipped with a reflux condenser, along with 0.15 gram sodium hydroxide. The mixture was heated to reflux with stirring. After forty minutes, a sample was taken from the organic phase and a sodium tridecanoate white crystalline solid formed therein upon cooling. The sample was acidified with sulfuric acid and solids were separated by filtration and washed three times with water. By gas chromatographic analysis it was determined that the material was 64.9% hydrolyzed, and that 97.5% of the tridecanoic acid was n-tridecanoic acids, representing a substantial enrichment from the original 65%. was subjected to partial hydrolysis under basic conditions The mixture was heated to reflux After forty minutes

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

Procedure: A solution of tridecanoic acid, methyl ester (24.63 g, 0.1078 mol), and anhydrous hydrazine (3.40 mL, 0.108 mol) in absolute ethanol (150 mL) was stirred at room temperature for 24 hours, then refluxed 2 days. The solution was allowed to cool, and the solid that crystallized was filtered off, washed, and dried in vacuo; yield 18.6 g (75%); mp 101°-104° C. refluxed 2 days to cool the solid that crystallized was filtered off washed dried in vacuo

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

Procedure: A solution of tridecanoic acid, methyl ester (24.63 g, 0.1078 mol), and anhydrous hydrazine (3.40 mL, 0.108 mol) in absolute ethanol (150 mL) was stirred at room temperature for 24 hours, then refluxed 2 days. The solution was allowed to cool, and the solid that crystallized was filtered off, washed, and dried in vacuo; yield 18.6 g (75%); mp 101°-104° C. refluxed 2 days to cool the solid that crystallized was filtered off washed dried in vacuo

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred autoclave was charged, at room temperature, with 67 g (728 mmol) of glycerol, 8.2 g (36 mmol) of methyl tridecylate, 0.82 g (10 wt %) of camphosulfonic acid and 0.74 g (1.0 mol %) of Pd/C at 5%. The autoclave was then pressurized at 50 bar of dihydrogen gas H2, and then it was heated at 140° C. for 24 h, stirring vigorously. After 24 h of reaction, the reaction mixture was brought back to room temperature. The catalyst was then filtered on a MILLIPORE® filter (a membrane filter) (0.45 μm) and was rinsed with absolute ethanol. The solvents were then evaporated and the organic products were extracted from the glycerol phase by extraction with CH2Cl2 (3×50 ml). The organic phase was washed with water (2×20 ml) and the CH2Cl2 was then evaporated at reduced pressure. The crude reaction product was analyzed by GC/MS. 1-O-tridecyl-glycerol ether was obtained at 16% GC yield. After 24 h of reaction was brought back to room temperature The catalyst was then filtered on a MILLIPORE® filter (a membrane filter) (0.45 μm) was rinsed with absolute ethanol The solvents were then evaporated the organic products were extracted from the glycerol phase by extraction with CH2Cl2 (3×50 ml) The organic phase was washed with water (2×20 ml) the CH2Cl2 was then evaporated at reduced pressure The crude reaction product

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

Procedure: A solution of tridecanoic acid, methyl ester (24.63 g, 0.1078 mol), and anhydrous hydrazine (3.40 mL, 0.108 mol) in absolute ethanol (150 mL) was stirred at room temperature for 24 hours, then refluxed 2 days. The solution was allowed to cool, and the solid that crystallized was filtered off, washed, and dried in vacuo; yield 18.6 g (75%); mp 101°-104° C. refluxed 2 days to cool the solid that crystallized was filtered off washed dried in vacuo