1: fish oil With potassium hydroxide; water in methanol T=55°C; 1.5 h; 2: methanol With sulfuric acid in water T=20 - 55°C; 1.5 h; Product distribution / selectivity;

1: With potassium hydroxide; water in methanol T=55°C; 1.5 h; 2: methanol With sulfuric acid in water T=20 - 55°C; 1.5 h; Product distribution / selectivity;

1.1: Ph3PBr2 / CH2Cl2 / 0.5 h / 20 °C 2.1: n-BuLi / hexane; tetrahydrofuran / 0.08 h / -78 °C 2.2: hexane; tetrahydrofuran / -78 °C 3.1: AcCl / 12 h / Heating View Scheme

1.1: LiAlH4 / diethyl ether / 2 h / 20 °C 2.1: Ph3PBr2 / CH2Cl2 / 0.5 h / 20 °C 3.1: n-BuLi / hexane; tetrahydrofuran / 0.08 h / -78 °C 3.2: hexane; tetrahydrofuran / -78 °C 4.1: AcCl / 12 h / Heating View Scheme

1.1: n-BuLi / hexane; tetrahydrofuran / 0.08 h / -78 °C 1.2: hexane; tetrahydrofuran / -78 °C 2.1: AcCl / 12 h / Heating View Scheme

1: fish oil With potassium hydroxide; water in methanol T=55°C; 1.5 h; 2: methanol With sulfuric acid in water T=20 - 55°C; 1.5 h; Product distribution / selectivity;

1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C / |Inert atmosphere 2: Dess-Martin periodane / dichloromethane / 1.5 h / |Inert atmosphere 3: methyl (triphenylphosphoranylidene)acetate / tetrahydrofuran / 2.5 h / |Reflux; |Inert atmosphere 4: copper(l) iodide; N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisobutylaluminium hydride / tetrahydrofuran / 4 h / 0 °C / |Inert atmosphere View Scheme

1: methyl (triphenylphosphoranylidene)acetate / tetrahydrofuran / 2.5 h / |Reflux; |Inert atmosphere 2: copper(l) iodide; N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisobutylaluminium hydride / tetrahydrofuran / 4 h / 0 °C / |Inert atmosphere View Scheme

acetyl chloride 12 h; Heating;

T=55°C; 1.5 h; Product distribution / selectivity;