The easiest way to do this is to treat chlorobenzene (C6H5-Cl) with Lithium Aluminum Hydride (LAH) in diethyl ether. 1st step: Dows process to convert Chlorobenzene to Phenol - This is most common reaction for Phenol synthesis - In this reaction, Chrolobenzene is hydrolyzed by strong base such as Sodium Hydroxide and water at high temperature (350 c) The catalyst is either aluminium chloride or iron. React it with CuCl (Sandmeyer’s Rxn) or Cu Powder (Gatterman Rxn) to form Chlorobenzene. The double bond electrons of the aromatic C=C act as a nucleophile, attacking the electrophilic Cl, and delocalization take place. Second step: Chloronium ion attack on the ring. Making chlorobenzene Benzene reacts with chlorine in the presence of a catalyst, replacing one of the hydrogen atoms on the ring by a chlorine atom. React Benzene with oleum (H2S2O7) to form benzenesulphonic acid, react it with NaOH/H+ to form Phenol. Diethyl ether boils about 35º C so it will be easier to separate the ether from the benzene. You could use tetrahydrofuran as solvent but the bp of THF and benzene (C6H6) are pretty close (66 and 80º C, respectively). Chlorobenzene to Benzene is a two step process. The reaction happens at room temperature. Third step: Proton transfer regenerates the aromatic character of the ring. First step: Chloronium ion formation, chlorine react with the Lewis acid to form a complex which makes the chlorine more electrophile. Add NaNO2 +HCl to form benzene Dizonium chloride.
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