Iodine → 1-(4'-Hydroxy-n-hexyl)-1-cyclohexanol

Participants

Reaction Steps

A solution of 1,5-dibromopentane (5.66 gms, 24.6 mmol) in dry THF (30 ml) was added slowly to a suspension of Magnesium turning (3.2 gms, 131 mmole) in dry THF (70 ml) and catalytic amount of iodine under nitrogen atmosphere. After the addition of about 5 ml of dibromopentane solution in THF, Grignard reaction was initiated. The addition was continued maintaining a gentle reflux. The mixture was refluxed for 18 hours to complete the formation of the Grignard reagent. To the reaction mixture was added a solution of a solution of lactone (20, 3 gms, 23.4 mmol) in dry THF (20 ml). The resulting mixture was refluxed for 10 hours under nitrogen and then quenched by addition of saturated solution of ammonium chloride at 0° C. The product was extracted in ethylacetate. Organic layer was washed with water, brine and dried over anh. Na2SO4. Drying agent was filtered off and the solvent was removed under vacuum to give 2.8 gms of diol (21), which was used without any further purification in the next step.

Provenance & Evidence