Sulfuric Acid → HCID 20281502, compound

Participants

Reaction Steps

A solution of methyl 4-(4-chlorophenyl)pent-4-enoate (5.8 g, prepared as described in Example 1) in dry diethyl ether (25 ml) was added to a stirred solution of methylmagnesium iodide [from methyl iodide (8.52 g) and magnesium turnings (1.7 g)] in dry diethyl ether (50 ml) (exotherm). After 1 hour at room temperature the reaction mixture was poured into a mixture of ice and dilute sulphuric acid, then extracted with diethyl ether. The extracts were washed with water, dried over magnesium sulphate, and concentrated under reduced pressure to give 2-(4-chlorophenyl)-5-hydroxy-5-methylhex-1-ene (5.8 g, quantitative) as a yellow oil, 1H nmr (CDCl3): δ1.22 (6H, singlet, CH3 ×2).

Provenance & Evidence