Synthesis of 2-(cyclohexen-1-yl)ethanol

Preparation of 2-(cyclohexen-1-yl)ethanol (2-(cyclohex-1-en-1-yl)ethanol; 2-(1-cyclohexenyl)-ethanol)

Preparation of 2-(cyclohexen-1-yl)ethanol (2-(cyclohex-1-en-1-yl)ethanol; 2-(1-cyclohexenyl)-ethanol)

Preparation of 2-(cyclohexen-1-yl)ethanol (2-(cyclohex-1-en-1-yl)ethanol; 2-(1-cyclohexenyl)-ethanol)

14 g of lithium wire and 500 ml anhydrous ethylamine are placed in a 500-ml three-necked flask fitted with a stirrer, a dropping funnel, and a reflux condenser with dry-ice cooling. All operations are conducted under an atmosphere of nitrogen. 48.8 g of  phenethyl alcohol is added with stirring during 8-10 hours. The initial blue color disappears fairly quickly and other color changes occur. At the end of the reaction time, the excess of lithium is removed with a tongs, and the mixture is decomposed by cautious addition of ammonium chloride to decoloration. The ethylamine is then distilled off and the residue is treated dropwise with water whilst cooling. The organic phase is removed in ether and dried over magnesium sulfate. Distillation at 74-75°/2 mm of the ethereal solution affords the 2-(cyclohexen-1-yl)ethanol in 67% yield.

R. A. Benkeser et al, J. Amer. Chem. Soc, 11, 3230, 6042 (1955)

IUPAC Name

2-(cyclohexen-1-yl)ethanol

InChI

InChI=1S/C8H14O/c9-7-6-8-4-2-1-3-5-8/h4,9H,1-3,5-7H2

InChI Key

UOAZYMOJIMTMHR-UHFFFAOYSA-N

Canonical SMILES

C1CCC(=CC1)CCO

Depositor-Supplied Synonyms

2-(cyclohex-1-en-1-yl)ethanol, NSC18902, AC1L5FFH, AC1Q7BSI, 1-Cyclohexene-1-ethanol, 2-(1-cyclohexenyl)-ethanol, 2-(cyclohexen-1-yl)ethanol, SCHEMBL953643, CTK1C6371, 2-(1-CYCLOHEXENYL)ETHANOL, AR-1C8816, NSC-18902, AKOS022504480

Removed Synonyms

CID227351, 3197-68-0, 3700-71-8

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