Synthesis of 1,6-heptadiene

Preparation of 1,6-heptadiene (hepta-1,6-diene)

Preparation of 1,6-heptadiene (hepta-1,6-diene)

Preparation of 1,6-heptadiene (hepta-1,6-diene)

Reduction in liquid ammonia is carried out in a cylindrical vessel of 3-liter capacity. This vessel is fitted with two ground necks at the top to take a dropping funnel and a stirrer, two glass tubes with taps for introduction and removal of ammonia, and a position for insertion of a cold-reading thermometer. Ammonia, pre-dried by soda lime and potassium hydroxide, is introduced with cooling by methanol and solid carbon dioxide and evacuation of the vessel and, whilst in the liquid state, freed from the last traces of moisture by small pieces of sodium. 101 g of 1,6-heptadiyne and 295 g of ammonium sulfate are added to 1 liter of liquid ammonia. Then 102 g of clean sodium are added in portions through a side arm, with stirring, until a permanent blue coloration is obtained. The crude 1,6-heptadiene is obtained in 87 % yield by the usual working up. After purification by distillation at 89-90° C yields 61 % (or 64.4 g) of 1,6-heptadiene (nD=1.4142).

A. L. Henne, K. W. Greenlee, J. Amer. Chem. Soc, 65, 2020 (1943)

IUPAC Name

hepta-1,6-diene

InChI

InChI=1S/C7H12/c1-3-5-7-6-4-2/h3-4H,1-2,5-7H2

InChI Key

GEAWFZNTIFJMHR-UHFFFAOYSA-N

Canonical SMILES

C=CCCCC=C

Depositor-Supplied Synonyms

1,6-HEPTADIENE, 3070-53-9, Hepta-1,6-diene, CH2=CH(CH2)3CH=CH2, GEAWFZNTIFJMHR-UHFFFAOYSA-N, ACMC-1CS8A, 258849_ALDRICH, AC1L291W, CTK1C4633, MolPort-003-928-727, ANW-26960, AKOS025295109, CJ-31800, KB-10699, TC-115705, FT-0607012, I14-59851, 3B3-034114

Removed Synonyms

CID16968, H0564

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