Preparation of propoxybenzene
To prepare the propoxybenzen, 0.25 g gramequivalent of metallic sodium is dissolved in 300 ml of absolute ethanol to which the phenol, dissolved in a little absolute ethanol is then added. After the addition of the 0.2 mole of propyl iodide (alternatively propyl bromide), the mixture is heated under reflux with stirring and exclusion of moisture for 5 hours. The alcohol is distilled off from the reaction mixture to a substantial extent through a 20-cm Vigreux column with stirring and the cooled distillation residue is poured into 100 ml of 5% caustic sodium carbonate; the organic phase is extracted several times with diethyl ether, washed with water, and dried with calcium chloride; the solvent is distilled off, and the residue is fractionated. Unchanged phenol can be recovered by acidifying the aqueous alkaline solution and extracting it with ether. The yield of propoxybenzen 80%, n20/D 1.5014; b.p. 81°C/12mm.
Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 208-210, (1973)
Propoxybenzene, Benzene, propoxy-, PHENYL PROPYL ETHER, Propyl phenyl ether, Propoxyphenyl, Ether, propyl phenyl, 622-85-5, Ether, phenyl propyl, EINECS 210-756-5, SBB061098, BRN 1634987, AI3-24227, 1-Phenoxypropane, AC1L1YYU, EBD48, SCHEMBL144684, CTK2F2924, DSNYFFJTZPIKFZ-UHFFFAOYSA-N, MolPort-000-219-452, ZINC2034347, ZINC02034347, AKOS002710506, AS01111, MCULE-2177440483, AN-46744, LS-67887, OR038310, OR304727, ST51047165, 4-06-00-00556 (Beilstein Handbook Reference), InChI=1/C9H12O/c1-2-8-10-9-6-4-3-5-7-9/h3-7H,2,8H2,1H