Synthesis of 1-hexanol

Preparation of 1-hexanol (n-hexyl alcohol)

Preparation of 1-hexanol (n-hexyl alcohol)

Preparation of 1-hexanol (n-hexyl alcohol)

1-liter three-necked flask is fitted with air tight stirrer, a 500 ml dropping funnel and a reflux condenser to the upper end of which a drying tube with anhydrous calcium chloride is attached. All parts of the glass apparatus must be dry. The flask is partially immersed in a bath of water and charged with 37.5 grams of magnesium turnings (the turnings are prepared by washing with a little absolute ether to remove surface grease, drying at 100-120° C, and allowing to cool in a desiccator) and a crystal of iodine in the flask. Separately in a dry vessel 161 ml (or 205.5 grams) of 1-bromobutane (n-butyl bromide) and 500 ml of absolute ether are mixed and introduced about 100 ml of the ether and 15 ml of the 1-bromobutane into the reaction flask. The water bath is slowly heated so that the ether refluxes gently in order to start the reaction. When the reaction has commenced the water bath is removed and sufficient amount of absolute ether is introduced with constant stirring to cover the magnesium. Then the remainder amount of the 1-bromobutane dissolved in the residual ether is introduced during 30-45 minutes. If the reaction becomes too vigorous, the flask is cooled in ice water. When all 1-bromobutane has been added the refluxing and stirring is continued for 15-20 minutes in order to complete the formation of the Grignard reagent.

Then the flask is cooled in a freezing mixture of ice and salt. The dropping funnel is removed and replace by a tube, 4 mm in diameter, the end of which is about 2 cm above the surface of the liquid. This delivery tube is attached to a flask, which is connected with “wash bottle” tubes, the long tube being nearer the three-necked flask and the other end being connected to a supply of dry nitrogen. The flask is cooled in a mixture of ice and salt and rapidly 90 grams of ethylene oxide are introduced from a sealed bulb of the reagent. The ethylene oxide must be cooled in an ice and salt before introducing to the reaction. Instead of adding the liquid ethylene oxide (b.p. 10.5° C), it may be dissolved in 100 ml of ice·cold anhydrous ether; this solution is added during 15-30 minutes. The yield, however, is somewhat lower. The ethylene oxide is gradually introduced into the reaction flask over a period of 1.5-2 hours. During this addition the temperature is maintained bellow 10° C. When all ethylene oxide has been added, the freezing mixture surrounding the three-necked flask is removed, the temperature of the mixture will gradually rise and the reaction mixture will boil gently. When boiling ceases, the reaction mixture is refluxed on a water bath for 30 minutes, then cooled to room temperature, and arranged for the distillation by insert a thermometer into a neck of the flask, fitting with condenser and a receiver.  250 ml of ether is collected in a measuring cylinder. The larger volumes of ether should be not collected as a violent reaction may set in, apparently due to a rearrangement of the initial reaction product, and considerable loss may ensue. Then the received is changed and 250 ml of anhydrous benzene are added into the reaction mixture. The distillation is continued with stirring until the temperature of the distilling vapor reaches 65° C. Then the mixture is boiled under reflux for 30 minutes; generally by this time the mixture has become so viscous that stirring is no longer very effective. The flask is cooled and decomposed by treating reaction mixture with 500 ml of an ice-water mixture. The precipitated magnesium hydroxide is dissolved with 30% sulfuric acid, then treated with sufficient amount of finely-crushed ice to keep the mixture cold. The mixture is steam distilled and about 2 liters of distillate are collected. The oily layer is separated, meanwhile, the aqueous layer is distilled until free of 1-hexanol and obtained the additional amount of 1-hexanol are combined. The crude 1-hexanol is stirred on a water bath with 250 ml of 20% sodium hydroxide solution, and steam distilled again as before, then dried with a little anhydrous calcium sulfate. Finally, 1-hexanol is purified by distillation through an efficient fractionating column, and collecting the fraction boiling at 154-157° C. The yield of 1-hexanol is 90 grams.

A text book of practical organic chemistry, by A. I. Vogel, 252-253, 1974

IUPAC Name

hexan-1-ol

InChI

InChI=1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3

InChI Key

ZSIAUFGUXNUGDI-UHFFFAOYSA-N

Canonical SMILES

CCCCCCO

MeSH Synonyms

1-hexanol, 1-hexanol, aluminum salt, 1-hexyl alcohol, n-hexanol

Depositor-Supplied Synonyms

1-Hexanol, Hexyl alcohol, Hexan-1-ol, HEXANOL, n-Hexanol, n-Hexyl alcohol, 111-27-3, 1-Hydroxyhexane, Amylcarbinol, Caproyl alcohol, 1-Hexyl alcohol, Pentylcarbinol, n-Hexan-1-ol, Caproic alcohol, C6 alcohol, EPAL 6, Alcohol(C6), Hexanol (VAN), Fatty alcohol(C6), Hexyl alcohol (natural), Alcohol C-6, Hexanol-(1), Caswell No. 482E, FEMA Number 2567, NSC 9254, UNII-6CP2QER8GS, HEXYL ALCOHOL, ACTIVE, FEMA No. 2567, HSDB 565, ZSIAUFGUXNUGDI-UHFFFAOYSA-N, EINECS 203-852-3, SBB059899, EPA Pesticide Chemical Code 079047, BRN 0969167, AI3-08157, DSSTox_CID_1931, DSSTox_RID_76410, DSSTox_GSID_21931, 25917-35-5, CAS-111-27-3, HE2, Caproalcohol, Hexalcohol, Hydroxyhexane, Hexanols, hexanol;, N-hexenol, Exxal 6, HEXANOL-CMPD, Exxal 6 (Salt/Mix), AC1Q2WFM, AC1Q2WFN, 6CP2QER8GS, AC1L1Q9T, n-C6H13OH, SCHEMBL1877, ACMC-1C26M, H13303_ALDRICH, WLN: Q6, KSC178E1L, MLS001055374, UN 2282 (Salt/Mix), BIDD:ER0298, CHEMBL14085, W256706_ALDRICH, W256714_ALDRICH, 442269_SUPELCO, 471402_ALDRICH, C6H14O, Jsp000849, 52828_FLUKA, 73117_FLUKA, CHEBI:87393, CTK0H8215, H13303_SIAL, HMDB12971, NSC9254, MolPort-001-779-716, 52828_SIAL, HMS3039L08, 23275-26-5 (aluminum salt), 471402_SIAL, ACN-S002388, NSC-9254, EINECS 247-346-0, Tox21_201335, Tox21_302953, ANW-16262, LMFA05000117, STL282713, UN2282, ZINC01699882, AKOS009031422, EBD2203383, LS-2366, MCULE-4299150163, NE10250, RL00460, RTR-002242, TRA0032352, NCGC00090949-01, NCGC00090949-02, NCGC00256385-01, NCGC00258887-01, AN-43058, CJ-06648, CJ-28634, Hexanols [UN2282] [Flammable liquid], SMR000677945, TR-002242, FT-0607887, ST51046167, EN300-19338, 81323-EP2269986A1, 81323-EP2272817A1, 81323-EP2301919A1, 81323-EP2305687A1, 81323-EP2371805A1, 81323-EP2380568A1, 89674-EP2272842A1, 89674-EP2292613A1, 89674-EP2305033A1, 4-01-00-01694 (Beilstein Handbook Reference), 3B4-0753, S14-1473, 3B1-002865, InChI=1/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H, 220713-27-9

Removed Synonyms

Hexahydrophenol, Hexalin, Capric alcohol, B-Nonylglucoside, Cyclohexan-1-ol, CYCLOHEXANOL, HEXANE, (s)-(+)-hexanol, 1-Hexanol, aluminum salt, 6-BROMOHEXAN-1-OL, CID8103, (Hydroxyethyloxy)tri(Ethyloxy)octane, H0130, C036260, BHL, HEX, 52019-78-0, BNG, C8E

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