Synthesis of 1-allylnaphthalene

Preparation of 1-allylnaphthalene

Preparation of 1-allylnaphthalene

Preparation of 1-allylnaphthalene

A Grignard reagent is prepared in customary manner from 207 g of 1-bromonaphthalene and 36 g of magnesium in 600 ml of ether (Org. Syntheses Coll. Vol. 1, 550 (1941)). The resulting solution of the Grignard reagent is added slowly with stirring to a solution of 121 g of allyl bromide in 250 ml. of benzene. The reaction mixture is stirred and heated under reflux for 2.5 hours, excess water is added, and the organic layer is separated and dried. Distillation gives 154 g of product boiling at 220-235° at atmospheric pressure. A second distillation through a 1-meter fractionating column gives 137 g. (81%) of 1-allylnaphthalene, b.p. 127.5-128.5°/8 mm.

J. Am. Chem. Soc., 60, 1662 (1938).

IUPAC Name

1-prop-2-enylnaphthalene

InChI

InChI=1S/C13H12/c1-2-6-11-8-5-9-12-7-3-4-10-13(11)12/h2-5,7-10H,1,6H2

InChI Key

RJFCFNWLPJRCLR-UHFFFAOYSA-N

Canonical SMILES

C=CCC1=CC=CC2=CC=CC=C21

Depositor-Supplied Synonyms

1-ALLYLNAPHTHALENE, 2489-86-3, 3-(1-Naphthyl)-1-propene, Naphthalene, 1-allyl-, alpha-Allylnaphthalene, Naphthalene, 1-(2-propenyl)-, 1-(2-Propenyl)naphthalene, BRN 1927776, 1-(2-propen-1-yl)-Naphthalene, 1-(prop-2-en-1-yl)naphthalene, prop-2-enylnaphthalene, ACMC-209vli, .alpha.-Allylnaphthalene, AC1Q2AAM, 1-prop-2-enylnaphthalene, AC1L29KB, 1-(2-propenyl)-naphthalene, KSC492M1H, CTK3J2613, MolPort-000-005-288, RJFCFNWLPJRCLR-UHFFFAOYSA-N, ZINC2036107, ANW-45220, AKOS006344680, AC-4946, MCULE-3947882115, RP10440, TRA0002515, VZ25904, Naphthalene, 1-(2-propenyl)- (9CI), AJ-33042, AK-88747, AN-11489, CJ-07542, CJ-31986, K920, KB-11081, LS-94430, OR002201, OR091105, DB-027358, RT-000822, ST2415130, 4CH-014460, FT-0634320, ST45022228, A18524, 3-05-00-01805 (Beilstein Handbook Reference), I14-0113, 3B3-015423

Removed Synonyms

CID17217, A2465

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