Synthesis of allyl chloride (3-chloro-1-propene)

Preparation of allyl chloride

The allyl chloride is prepared from allyl alcohol according to the following method:

Preparation of allyl chloride (3-chloro-1-propene)

Preparation of allyl chloride (3-chloro-1-propene)

Allyl alcohol is placed in the flask fitted with a reflux condenser with three times its weight of hydrochloric acid, (d=1.20) and heated for one hour on a water bath. The above amount of hydrochloric acid constitutes about two molecules of hydrochloric acid to each molecule of allyl alcohol. The flask is cooled and the dark layer which separates in the top is removed and distilled. Allyl chloride distills at 46-50° C (the boiling point of pure allyl chloride is 46° C) yielding about 100 g of pure final product. Allyl chloride is a pleasant smelling liquid bearing a slightly yellow color.

The synthesis of amino acids, by B. B. Wilcox, 22, 1904

If copper(I) chloride is employed as a catalyst the yield of allyl chloride exceeds over 90%.

Preparation of allyl chloride by using copper(I) chloride as a catalyst

Preparation of allyl chloride by using copper(I) chloride as a catalyst

100 ml of allyl alcohol, 150 ml of concentrated hydrochloric acid and 2 grams of freshly prepared copper(I) chloride are placed in a 1000 ml round-bottomed flask equipped with a reflux condenser. The flask is cooled in an ice-water bath and 50 ml of concentrated sulfuric acid are added dropwise through the condenser with the frequent shaking of the flask. A little hydrogen chloride may be evolved towards the end of the reaction and the reaction mixture is left for 30 minutes in order to complete the separation of the allyl chloride. The upper layer of crude allyl chloride is separated, washed with twice its volume of water, and dried over anhydrous calcium chloride. Allyl chloride is purified by distillation, the fraction passing over at 46-47° C is collected yielding yield over 90% of pure allyl chloride.

A text book of practical organic chemistry, by A. I. Vogel, 276, 1974

IUPAC Name

3-chloroprop-1-ene

InChI

InChI=1S/C3H5Cl/c1-2-3-4/h2H,1,3H2

InChI Key

OSDWBNJEKMUWAV-UHFFFAOYSA-N

Canonical SMILES

C=CCCl

MeSH Synonyms

allyl chloride

Depositor-Supplied Synonyms

ALLYL CHLORIDE, 3-Chloro-1-propene, 1-Propene, 3-chloro-, 3-chloroprop-1-ene, 107-05-1, 3-Chloropropylene, 3-Chloropropene, Chlorallylene, 2-Propenyl chloride, 3-Chloropropene-1, Allylchlorid, Chloroallylene, 1-Chloro-2-propene, Propene, 3-chloro-, 3-Chlorpropen, 3-Chloro-1-propylene, Chloropropene, NCI-C04615, Chloro-2-propene, Allile(cloruro di), 1-Chloropropene-2, alpha-Chloropropylene, Allyle(chlorure d’), Allylchlorid [German], 3-Chlorpropen [German], NSC 20939, UNII-V2RFT0R50S, p-Aminopropiofenon [Czech], CCRIS 19, HSDB 178, Allile (cloruro di) [Italian], Allyle (chlorure d’) [French], CHEBI:82379, OSDWBNJEKMUWAV-UHFFFAOYSA-N, EINECS 203-457-6, UN1100, BRN 0635704, allylchloride, allyl-chloride, Chlo roallylene, 3-Chloroprene, p-Aminopropiofenon, 3-Chloro propene, 1-chloro propene-2, Allile (cloruro di), Allyle (chlorure d’), .alpha.-Chloropropylene, Chloropropene (Related), ACMC-1BTGY, DSSTox_CID_45, CH2=CHCH2Cl, AC1L1PP0, DSSTox_RID_79426, V2RFT0R50S, DSSTox_GSID_39231, A30702_ALDRICH, KSC175I0H, WLN: G2U1, 236306_ALDRICH, 442446_SUPELCO, 481378_ALDRICH, CHEMBL451126, Jsp000627, A30702_SIAL, CTK0H5403, MolPort-001-767-892, LTBB001173, NSC20939, STR01272, Tox21_200824, ANW-15474, LS-424, NSC-20939, STL283938, AKOS000119803, RP18365, RTR-001376, UN 1100, NCGC00091097-01, NCGC00091097-02, NCGC00258378-01, AN-22462, CAS-107-05-1, KB-47201, SC-47190, DB-029431, TR-001376, FT-0615299, Allyl chloride [UN1100] [Flammable liquid], Allyl chloride [UN1100] [Flammable liquid], C19316, InChI=1/C3H5Cl/c1-2-3-4/h2H,1,3H, 4-01-00-00738 (Beilstein Handbook Reference), 3B4-1347, I14-5814, 36813-24-8

Removed Synonyms

1-Chloropropylene, CID7850, c0274, C023698

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