Synthesis of 2-fluoroethanol

Preparation of 2-fluoroethanol

Preparation of 2-fluoroethanol

Preparation of 2-fluoroethanol

322 g of ethylene chlorohydrin are dropped during 3 hours into a mixture of 350 g of dry, powdered potassium fluoride, 230 g of ethylene glycol, and 130 g of diethylene glycol stirred at 170-180° C, the 2-fluoroethanol (b.p. 97-104° C) being distilled off continuously through a 30-cm column. A slow stream of air is subsequently drawn through the apparatus to complete removal of the 2-fluoroethanol. The crude product (152.5 g) is set aside over sodium fluoride to remove traces of hydrogen fluoride and is then redistilled, yielding 42.5 % yield (or 109 g) of 2-fluoroethanol.

J. Amer. Chem. Soc, 70, 2596 (1948).

J. Org. Chem., 15, 425 (1950).

2-Fluoroethanol may also be obtained from ethylene chlorohydrin and potassium fluoride in glycerol at 50-60°C (Acta Chim. Acad. Sci. Hung., 3, 199 (1953)) or without a solvent in an autoclave at 130-135°C (J. Chem. Soc, 1949, 773)

IUPAC Name

2-fluoroethanol

InChI

InChI=1S/C2H5FO/c3-1-2-4/h4H,1-2H2

InChI Key

GGDYAKVUZMZKRV-UHFFFAOYSA-N

Canonical SMILES

C(CF)O

MeSH Synonyms

2-fluoroethanol, 2-fluoroethanol, sodium salt, fluoroethanol

Depositor-Supplied Synonyms

2-Fluoroethanol, 371-62-0, Ethanol, 2-fluoro-, Fluoroethanol, 2-Fluoro-1-ethanol, ETHYLENE FLUOROHYDRIN, Monofluorethanol, Monofluoroethanol, beta-Fluoroethanol, 2-Fluoro-ethanol, TL 741, .beta.-Fluoroethanol, 2-fluoroethan-1-ol, ETHANOL, FLUORO-, HSDB 6389, GGDYAKVUZMZKRV-UHFFFAOYSA-N, EINECS 206-740-2, NSC 158283, BRN 1730857, Ethylene fluorhydrin, Ethanol,2-fluoro-, Ethylene fluorohydrine, ACMC-209ira, CH2FCH2OH, AC1L1TPD, 2-Fluoro-1-hydroxyethane, AC1Q4OU9, WLN: Q2F, ETHOXY, 2-FLUORO-, UNII-4M427A5HML, KSC489M6J, 160342_ALDRICH, 4M427A5HML, CHEMBL115586, Jsp006589, 46460_FLUKA, CTK3I9664, MolPort-001-771-679, BB_SC-0430, ACT09629, ANW-28580, AR-1E1769, BBL027407, NSC158283, RW2123, STK802058, ZINC43352750, AKOS004904101, LS40655, MCULE-7590677201, NSC-158283, RTR-015126, TRA0063580, AN-44602, BP-11368, KB-24192, LS-66790, LS-66791, OR034240, OR198499, OR263914, TR-015126, FT-0612432, EN300-82361, InChI=1/C2H5FO/c3-1-2-4/h4H,1-2H, 4-01-00-01366 (Beilstein Handbook Reference), 3B4-0827, I14-1876, W-106565

Removed Synonyms

2-Methylserotonin HCl, CID9737, 10030-52-1, 63919-01-7, 65072-34-6, 78263-90-8

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