**(E/Z) 1,3-Dimethoxy-5-(Prop-1-en-1-yl) benzene (2)**

3,5-dimethoxylbenzyltriphenylphosphonium bromide (**1**) (2 g, 4 mmol) in aqueous K2CO3 solution (0.1 M, 50 mL) and acetaldehyde (0.264 g, 0.337 mL, 6 mmol) were refluxed for 24 h, cooled to room temperature and cyclohexane (50 mL) was added and vigorously shaken for 30 min. The mixture was filtered, and the aqueous layer was extracted with cyclohexane (2 × 50 mL). Combined organic layers were dried over MgSO4, filtered, and evaporated. The crude olefin, **2** was purified on a silica gel column using Hexane: EtOAc (95:0.5) as an eluent to give mixture of olefins, **2** in 50% yield. 1H NMR (500 MHz, CDCl3): δ 6.50 (d, 2H, aromatic, J = 2.0 Hz), 6.39–6.30 (m, 1H), 6.28–6.11 (m, 2H), 3.80 (s, 6H, OCH3), and 1.87 (dd, 3H, CH3, J = 6.5 Hz).

#### **(E/Z) 1,3-Dimethoxy-5-(Butyl-1-en-1-yl) benzene (3)**

A mixture of olefins (E/Z)—**3** was prepared as described for olefin **2** using 3,5 dimethoxybenzyltriphenylphosphonium bromide (**1**) (4.0 g, 8 mmol) and propionaldehyde (0.69 g, 0.86 mL, 12 mmol) to give **3** in 91% yield. 1H NMR (500 MHz, CDCl3): δ 6.51 (d, 2H, aromatic, J = 2.5 Hz), 6.33 (d, 1H, aromatic, J = 2.5 Hz), 5.95–5.75 (m, 2H, CH), 3.80 (s, 6H, OCH3), 2.70–2.50 (m, 2H, CH2), 1.57–1.12 (m, 4H, CH2) and 1.12–1.00 (m, 3H, CH3).

### **(E/***Z***) 1,3-Dimethoxy-5-(Heptyl-1-en-1-yl) benzene (4)**

Olefins (E/Z)—**4** was prepared as described for **2** using 3,5-dimethoxybenzyltriphenylphosphonium bromide (**1**) (4.0 g, 8 mmol) and hexanaldehyde (1.2 g, 1.48 mL, 12 mmol) to give **4** in 56% yield. 1H NMR (500 MHz, CDCl3): δ 6.41–6.20 (m, 2H, aromatic), 5.95–5.75 (m, 2H, CH), 3.97 (s, 6H, OCH3), 3.97 (s, 6H, OCH3), 2.32 (m, 2H, CH2), 1.46 (q, 2H, CH2, J = 7.5 Hz), 1.41–1.20 (m, 4H, CH2), and 0.96–0.88 (m, 3H, CH3).

#### **(E/***Z***)-1,3-Dimethoxy-5-(nonyl-1-en-1-yl) benzene (5)**

A mixture of olefins (E/Z)—**5** was prepared as described for **2** using 3,5-dimethoxybenzyltriphenylphosphonium bromide (**1**) (2.0 g, 4 mmol), and octanaldehyde (0.77 g, 0.94 mL, 6 mmol) to give olefin **5** in 95% yield. 1H NMR (500 MHz, CDCl3): δ 6.54 (d, 1H, J = 2.0 Hz) 6.47 (d, 1H, J = 2.0 Hz), 6.39–6.30 (m, 2H), 6.28–6.20 (m, 1H), 3.82 (s, 6H, OCH3), 2.40–2.32 (m, 1H), 2.25–2.20 (m, 1H),1.55–1.25 (m, 10H, CH2), and 0.92 (dd, 3H, CH3, J = 13.5 Hz and 6.5 Hz).

#### **1,3-Dimethoxy-5-propylbenzene (6)**

A mixture of **2** (1.00 g, 5.62 mmol) in EtOH (60 mL) and 10% Pd/C (100 mg) under 40psi of H2 atmosphere were shaken in Parr Hydrogenation apparatus for 24 h. The catalyst was removed by filtration over Celite and the solvent was evaporated under reduced pressure to give compound **6** in 88% yield; 1H NMR (500 MHz, CDCl3): δ 6.38 (d, 2H, aromatic, J= 2.0 Hz), 6.34 (t, aromatic, J = 2.0 Hz), 3.81 (s, 6H, OC*H*3), 2.57 (q, 2H, CH2, *J* = 7.5 Hz), 1.69–1.62 (m, 2H, CH2), and 0.97 (t, 3H, CH3,J-= 7.5 Hz).
