Synthesis of 1,2-dimethyl-1,4-cyclohexadiene

Preparation of 1,2-dimethyl-1,4-cyclohexadiene

1,2-dimethyl-1,4-cyclohexadiene is prepared by reduction of o-xylene with sodium in liquid ammonia.

Preparation of 1,2-dimethyl-1,4-cyclohexadiene

Preparation of 1,2-dimethyl-1,4-cyclohexadiene

A mixture of 54 grams of o-xylene and 51 grams of anhydrous methanol is dropped slowly into a solution of 30 grams of sodium in 400 ml of liquid ammonia at —70 °C to —65° C, and the whole is stirred until the blue color is discharged. The ammonia is then evaporated, the residue is treated with water, and the hydrocarbon mixture is separated. The dihydro-o-xylene can be purified by treating with bromine to form the di- or the tetra-bromide of dihydro-o-xylene. For the preparation of 1,2-dimethyl-1,4-cyclohexadiene,  reduction procedure is repeated leading to  91 % yield.

Chem. Ber., 88, 388, 346, 1955

IUPAC Name

1,2-dimethylcyclohexa-1,4-diene

InChI

InChI=1S/C8H12/c1-7-5-3-4-6-8(7)2/h3-4H,5-6H2,1-2H3

InChI Key

QBSFOUVYWBJKBF-UHFFFAOYSA-N

Canonical SMILES

CC1=C(CC=CC1)C

Depositor-Supplied Synonyms

1,2-Dimethyl-1,4-cyclohexadiene, 1,4-Cyclohexadiene, 1,2-dimethyl-, 17351-28-9, AC1L3GHV, QBSFOUVYWBJKBF-UHFFFAOYSA-N, 1,2-dimethylcyclohexa-1,4-diene, 1,2-dimethyl-cyclohexa-1,4-diene, AKOS006272088

Removed Synonyms

CID140223

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