Synthesis of 2-chloroethyl ethyl ether

Preparation of 2-chloroethyl ethyl ether

A mixture of 1 mole of dry pyridine (or dimethylaniline, quinoline, etc) and 1 mole of 2-ethoxyethanol is cooled to —20° C and 1.1 mole thionyl chloride is added, with stirring, at such a rate that the temperature does not exceed 0° C. The mixture is allowed to come to room temperature and then kept at 100° C for 2 hours. The product is cooled and treated with dilute hydrochloric acid, and the 2-chloroethyl ethyl ether is taken up in ether, washed with dilute sodium hydroxide solution and with water, and dried over sodium sulfate, yielding 61-84%. Purification could be performed by distillation collecting fraction boiling at 107 °C.

J. Chem. Soc, 1950, 406





InChI Key


Canonical SMILES


Depositor-Supplied Synonyms

2-Chloroethyl ethyl ether, 628-34-2, 1-CHLORO-2-ETHOXYETHANE, 2-Ethoxyethyl chloride, 2-Chloroethoxyethane, 2-Chloroethylethylether, Ether, 2-chloroethyl ethyl, 1-chloro-2-ethoxy-ethane, beta-Chloroethyl ethyl ether, Ethyl beta-chloroethyl ether, Ethane, 1-chloro-2-ethoxy-, CCRIS 9095, GPTVQTPMFOLLOA-UHFFFAOYSA-N, EINECS 211-037-9, SBB061015, BRN 1731361, 2-chloro-1-ethoxyethane, chloroethylethyl ether, 2-Chlorodiethyl ether, PubChem1932, (2-chloroethoxy)ethane, beta-Chlorodiethyl ether, 2-chloroethylethyl ether, ACMC-1AXDY, AC1L1ZDU, 2-chloroethyl-ethyl ether, Ethane,1-chloro-2-ethoxy-, 1-chloranyl-2-ethoxy-ethane, C41207_ALDRICH, KSC498A2J, SCHEMBL115596, .beta.-Chloroethyl ethyl ether, Ethyl .beta.-chloroethyl ether, 23020_FLUKA, CTK3J8024, MolPort-003-928-115, ZINC2031622, ANW-34402, ZINC02031622, AKOS009157288, Ethane, 1-chloro-2-ethoxy- (9CI), MCULE-1290576729, TRA0001706, VZ34632, AN-46905, BC214993, CJ-31764, KB-22833, LP050913, LS-67793, OR021589, AB0057554, DB-054301, RT-004180, TL8004282, C1172, FT-0632655, ST51047095, A834031, I14-6004, 3B3-035889

Removed Synonyms

2-Chloroethyl ether, 2-chloroethylether, CID12341, 4-01-00-01375 (Beilstein Handbook Reference), 29110-48-3

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