tetradecan-1-ol

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

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

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

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

Procedure: Compound (3) (0.500 g, 1.66 mmol) was weighed into a flame-dried 2-neck flask fitted with a condenser. Toluene (17 mL), 1-tetradecanol (1.42 g, 6.64 mmol), and p-toluenesulfonic acid (0.063 g, 0.332 mmol) were then added. The mixture was placed in a 130° C. heat bath and stirred overnight. The mixture was diluted with water, extracted with dichloromethane, dried over MgSO4, filtered, and concentrated. The product was purified via column chromatography (20% dichloromethane in hexanes) to yield compound (4b) as a yellow solid (0.540 g, 49%). 1H NMR (500 MHz, CDCl3, 298 K): 8.48 (s, 2H); 7.47 (m, 4H); 4.38 (t, J=6.6 Hz, 4H); 2.02 (quintet, J=7.7 Hz, 4H); 1.65 (quintet, J=7.8 Hz, 4H); 1.39 (m, 40H); 0.89 (t, J=7.1 Hz 6H) ppm. 13C NMR (125 MHz, CDCl3, 298 K): 149.74; 139.68; 128.05; 127.36; 124.87; 124.64; 110.97; 73.54; 31.96; 30.66; 29.73; 29.70; 29.54; 29.40; 26.18; 22.73; 14.17 ppm. HRMS (ESI-TOF-MS): m/z calcd for C42H64O2S2 664.4348, found 664.4356. fitted with a condenser was placed in a 130° C. heat bath extracted with dichloromethane dried over MgSO4 filtered concentrated The product was purified via column chromatography (20% dichloromethane in hexanes)

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

Procedure: 1-tridecanol; 1-tetradecanol; 1-pentadecanol; 1-hexadecanol;

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

Procedure: Prepared from the glycidyl ether of tetradecanol.

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

Procedure: A mixture of 21.4 g (0.100 mole) of 1-tetradecanol, 5.9 g (0.146 mole) of sodium hydride (59.5% in oil) and 300 ml of dried xylene is heated to reflux with stirring for 2 hours then allowed to cool after which 7.5 g (0.046 mole ) of 5-chloro-2-thiophenecarboxylic acid is added. The mixture is refluxed for 64 hours after which the mixture is cooled and poured into a water-ice mixture, acidified with acetic acid, and extracted with the addition of ether. The ether is evaporated and aqueous layer extracted 5 times with water: strong ammonia solution (1:1). The combined aqueous extract is acidified with acetic acid. The solid obtained is crystallized twice from hexane to give 5-(tetradecyloxy)-2-thiophene carboxylic acid, M.P. 95°-96° C. is heated to reflux is added The mixture is refluxed for 64 hours after which the mixture is cooled extracted with the addition of ether The ether is evaporated aqueous layer extracted 5 times with water The combined aqueous extract The solid obtained is crystallized twice from hexane

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

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

Procedure: One mole of tetradecanol ethoxylated with 2 moles of ethylene oxide per mole of tetradecanol and one mole of epichlorohydrin were reacted in the presence of tin tetrachloride at a temperature of 60 to 70° C. and a glycidyl ether was obtained. A solution of 30% sodium hydroxide in water was added at 80° C. After 30 minutes under vigorous stirring at 80° C., the resulting glycidyl ether was separated from the water phase. It had the structure

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

Procedure: One mole of tetradecanol ethoxylated with 2 moles of ethylene oxide per mole of tetradecanol and one mole of epichlorohydrin were reacted in the presence of tin tetrachloride at a temperature of 60 to 70° C. and a glycidyl ether was obtained. A solution of 30% sodium hydroxide in water was added at 80° C. After 30 minutes under vigorous stirring at 80° C., the resulting glycidyl ether was separated from the water phase. It had the structure

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

Procedure: Propylene oxide was bubbled into 685 g of myristyl alcohol in the presence of potassium hydroxide catalyst until three moles of propylene oxide were added per mole of myristyl alcohol, thus obtaining a pale, yellow liquid (PPG-3 myristyl ether) as the major product.

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

Procedure: One mole of tetradecanol ethoxylated with 2 moles of ethylene oxide per mole of tetradecanol and one mole of epichlorohydrin were reacted in the presence of tin tetrachloride at a temperature of 60 to 70° C. and a glycidyl ether was obtained. A solution of 30% sodium hydroxide in water was added at 80° C. After 30 minutes under vigorous stirring at 80° C., the resulting glycidyl ether was separated from the water phase. It had the structure