pentadecane-1,15-diol

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: Lithium aluminium hydride (1.52 g, 40.0 mmol, 2.0 eq.) was suspended in dry THF (80 mL) under an argon atmosphere. A solution of 15-pentadecanolide (4.80 g, 20.0 mmol) in dry THF (200 mL) was added at 0° C. Stirring was continued at this temperature for 1 h and for 3 more hours at r.t. Potassium sodium tartrate solution (20%, 50 mL) was added dropwise to the stirred reaction mixture. The phases were separated and the aqueous phase was extracted with diethyl ether (3×100 ml). The combined organic layers were dried over MgSO4. The solvent was removed in vacuo and the product was isolated as a white solid, which was used for the next step without purification. Yield: 4.68 g (96%). The phases were separated the aqueous phase was extracted with diethyl ether (3×100 ml) The combined organic layers were dried over MgSO4 The solvent was removed in vacuo the product was isolated as a white solid, which was used for the next step without purification

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: A 54 g portion of the hydrogenated product obtained in Reference Example 2 and 0.2 g of magnesium oxide were put into the same apparatus of Inventive Example 1 and the reaction was carried out under conditions of 230 to 260° C. and 1.3 kPa to 130 Pa to obtain 15.2 g of a colorless liquid distillate 3 hours thereafter. This distillate contained 2.2 g of cyclopentadecanolide (yield 94%), 0.93 g of 1,15-pentadecanediol (recovery ratio 96%) and 11.3 g of 2-decyl-1-tetradecanol. The reaction residue was a light yellow liquid having a viscosity of 85 mPa·s, and 28.4 g of di-2-decyl-1-tetradecyl pentadecandioate was recovered from the residue (recovery ratio 85%).

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

Procedure: Lithium aluminium hydride (1.52 g, 40.0 mmol, 2.0 eq.) was suspended in dry THF (80 mL) under an argon atmosphere. A solution of 15-pentadecanolide (4.80 g, 20.0 mmol) in dry THF (200 mL) was added at 0° C. Stirring was continued at this temperature for 1 h and for 3 more hours at r.t. Potassium sodium tartrate solution (20%, 50 mL) was added dropwise to the stirred reaction mixture. The phases were separated and the aqueous phase was extracted with diethyl ether (3×100 ml). The combined organic layers were dried over MgSO4. The solvent was removed in vacuo and the product was isolated as a white solid, which was used for the next step without purification. Yield: 4.68 g (96%). The phases were separated the aqueous phase was extracted with diethyl ether (3×100 ml) The combined organic layers were dried over MgSO4 The solvent was removed in vacuo the product was isolated as a white solid, which was used for the next step without purification

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