(E)-2-methyltetradeca-1,3-diene could be produced through the following synthetic routes.

(E)-2-Methyltetradeca-1,3-diene. Caution! tert-Butyllithium is extremely pyrophoric and care must be taken to avoid exposure to air at all times. A 2-L, single-necked, round-bottomed flask is equipped with a magnetic stirrer bar and a rubber septum pierced by an argon inlet needle and an outlet needle. The flask, in which a positive flow of argon is maintained throughout the entire procedure, is flame-dried under argon, allowed to cool, and then charged by syringe with dry tetrahydrofuran (75 mL) and 2-bromopropene (6.24 mL, 70.2 mmol, 1.30 equiv). The solution is cooled to -78 °C (bath temperature) in a dry ice/acetone bath and then a 1.58 M solution of tert-butyllithium in pentane (89.2 mL, 140 mmol, 2.6 equiv) is added dropwise by syringe over 20 min in ten roughly equal portions. The resulting bright-yellow suspension is stirred for 10 min at -78 °C, then an additional portion of 2-bromopropene (0.65 mL, 7.3 mmol, 0.14 equiv) is added dropwise over 7 min. The resulting pale-yellow suspension is stirred for an additional 30 min at -78 °C (during which time the preparation of the lithium 2,2,6,6-tetramethylpiperidide (LTMP) solution is initiated) and is warmed to 0 °C by transfer into an ice bath for 10 min. The resulting pale-yellow solution is re-cooled to -78 °C (bath temperature).

A 1-L, single-necked, round-bottomed flask is equipped with a magnetic stirrer bar and a rubber septum pierced by an argon inlet needle and an outlet needle. The flask, in which a positive flow of argon is maintained throughout the entire procedure, is flame-dried under argon, then is charged with dry pentanes (800 mL) and 2,2,6,6-tetramethylpiperidine (18.2 mL, 108 mmol, 2.0 equiv) by syringe. The colorless solution is cooled to 0 °C in an ice bath and then a 1.57 M solution of n-butyllithium in hexanes (68.8 mL, 108 mmol, 2.0 equiv) is added dropwise by syringe over 15 min in seven roughly equal portions. The resulting yellow LTMP solution is stirred at 0 °C for 30 min further and then is added via cannula over 15 min to the stirring pale-yellow suspension of 2-propenyllithium at -78 °C. The resulting yellow suspension is transferred to an ice bath, is stirred for 30 min and then 1,2-epoxydodecane (11.8 mL, 54.0 mmol) is added dropwise by syringe in three roughly equal portions over 5 min. The ice bath is removed and the resulting yellow suspension is stirred for 2 h.

The bright-yellow solution is re-cooled to 0 °C and 50 mL of a 1 M aqueous hydrochloric acid solution is added by syringe over 5 min. The reaction mixture is poured into a 3-L separatory funnel containing 1 M aqueous hydrochloric acid solution (200 mL). The reaction flask is rinsed with diethyl ether (2 × 100 mL), which is added to the separatory funnel. After thorough mixing, the aqueous layer is separated and extracted with diethyl ether (3 × 200 mL). The combined organic extracts are washed with brine (200 mL), dried over magnesium sulfate, filtered and evaporated under gradually reduced pressure (40 °C, 760 mmHg to 15 mmHg) using a rotary evaporator to leave 18.6 g of a pale-yellow residue.

The yellow residue is loaded neat onto a pad of silica gel (15 cm × 6 cm) that has already been wetted with n-pentane, and the flask is rinsed with pentane (2 × 10 mL). The pad is rinsed with 1000 mL of n-pentane and the eluent is collected directly as a single fraction. Rotary evaporation under reduced pressure (40 °C, 760 mmHg to 15 mmHg) for 2 h gives 6.47 g (58%) of (E)-2-methyltetradeca-1,3-diene as a colorless oil. The E/Z ratio of this product is determined to be 97:3.

Notice: tert-Butylithium is extremely pyrophoric and must not be allowed to come into contact with the atmosphere. This reagent should only be handled by individuals trained in its proper and safe use. It is recommended that transfers be carried out by using a 20-mL or smaller glass syringe filled to no more than 2/3 capacity, or by cannula. For a discussion of procedures for handling air-sensitive reagents, see Aldrich Technical Bulletin AL-134.