Synthesis of 3-methylbuta-1,2-diene

Preparation of 3-methylbuta-1,2-diene

Preparation of 3-methylbuta-1,2-diene

Preparation of 3-methylbuta-1,2-diene

To a flask cooled to -30°C to -40°C and containing 20.0 g (0.11 mole) of 1,1-dichloro-2-ethoxy-3,3-dimethylcyclopropane in 30 ml of dry ether is added dropwise 100 ml of a 1.3 M ethereal n-methyllithium solution (0.13 mole) over a 1 hours period. The reaction mixture is then stirred for an additional 0.5 hours while it is warmed to room temperature. Water is added, the ether is separated, washed with water, dried over sodium carbonate, and then fractionally distilled to afford 7.3 g (59 %) of impure 3-methylbuta-1,2-diene, b.p. 55°-57°C (65 mm), nD 1.4344 at 24°C. Redistillation gives a pure product, b.p. 51°C (60 mm), nD 1.4400 at 24°C.

L. Skattebol, J. Org. Chem. 31, 1554 (1966).

IUPAC Name

3-methylbuta-1,2-diene

InChI

InChI=1S/C5H8/c1-4-5(2)3/h1H2,2-3H3

InChI Key

PAKGDPSCXSUALC-UHFFFAOYSA-N

Canonical SMILES

CC(=C=C)C

MeSH Synonyms

3-methyl-1,2-butadiene

Depositor-Supplied Synonyms

3-METHYL-1,2-BUTADIENE, 1,1-Dimethylallene, 598-25-4, 3-Methylbuta-1,2-diene, 3,3-Dimethylallene, 1,1-Dimethylallylene, 2-Methyl-2,3-butadiene, 1,2-Butadiene, 3-methyl-, PAKGDPSCXSUALC-UHFFFAOYSA-N, NSC74117, ACMC-1AQBC, AC1L1XYR, 110930_ALDRICH, CH2=C=C(CH3)2, CTK5B0556, ZINC1699502, EINECS 209-926-1, ANW-33362, NSC 74117, NSC-74117, AKOS015916541, AK176348, AN-24976, OR034823, 1,2-Butadiene, 3-methyl- (8CI)(9CI), TC-122107, FT-0616028, M0621, 1,2-Butadiene,3-methyl- (6CI,7CI,8CI,9CI), InChI=1/C5H8/c1-4-5(2)3/h1H2,2-3H, I14-50002, 3B1-006535

Removed Synonyms

1, 3-methyl-, CID11714

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