Preparation of butoxybenzene
To prepare the butoxybenzene (butyl phenyl ether), 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 butyl iodide (alternatively butyl 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 at 87°C/9mm. Unchanged phenol can be recovered by acidifying the aqueous alkaline solution and extracting it with ether. The yield of butoxybenzene 80%, n20/D 1.497; b.p. 210.3 °C; m.p. −19 °C; d=0.935 g/mL at 25 °C.
Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 208-210, (1973)
Butoxybenzene, BUTYL PHENYL ETHER, n-Butyl phenyl ether, 1126-79-0, Benzene, butoxy-, Ether, butyl phenyl, Phenyl butyl ether, Butoxyphenyl, n-Butoxybenzene, (butyloxy)benzene, YFNONBGXNFCTMM-UHFFFAOYSA-N, NSC 8467, EINECS 214-426-1, SBB060061, BRN 1635559, AI3-00446, butoxy-benzene, 1-Phenoxybutane, n-butyloxybenzene, n-Butylphenylether, PubChem12529, ACMC-2099fz, AC1L23KG, WLN: 4OR, SCHEMBL36192, 142344_ALDRICH, Jsp000979, UNII-H804A5426K, CTK0H5356, NSC8467, MolPort-000-152-600, LABOTEST-BB LTBB001335, NSC-8467, ZINC1586758, ANW-16509, ZINC01586758, AKOS002710507, AS01104, H804A5426K, MCULE-6049343059, AN-48648, CJ-25305, KB-75823, LP068132, LS-67784, OR011112, SC-69204, DB-041112, TC-105254, B0927, FT-0623298, ST50824233, X7903, 4-06-00-00558 (Beilstein Handbook Reference), I01-19744, 3B3-023519
Butylthiobenzene, C10H14O, CID14311