Hydrochloric Acid → Methyl 4-(5-Hydroxypent-1-en-2-yl)benzoate

Reaction equation

C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=[CH2:15])(=O)C.Cl>CO>[OH:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=1)=[CH2:15]

Participants

Procedure

To a solution containing 0.52 g (1.0 eq) of dry potassium carbonate in 100 ml of anhydrous methanol was added 1.0 g (1.0 eq) of methyl 4-(5-acetoxy-pent-1-en-2-yl)benzoate in anhydrous methanol. The resulting reaction mixture was stirred for two hours at room temperature, neutralized by the addition of 7.6 ml of 1N hydrochloric acid (2.0 eq), and extracted twice with dichloromethane. The extracts were dried over magnesium sulfate, and concentrated under reduced pressure to yield the product. mp. 28-30° C. M.S.:m/z= 220.1094, (M+ calc. for CH13H16O3 : 220.1099), 189 (M+ --CH3) ), 176 (100%), 145. 1H-N M.R.(CDCl3, 300 MHz): δ=1.56(s (broad), 1H, OH); 1.75(quin, 2H, CH2 --CH2 --CH2, J=7.5 Hz); 2.60(t, 2H, CH2 --C=, J=7.5 Hz); 3.68(t, broad), 2H, CH2OH, J=7.5 Hz; 3.94(s, 3H, CH3O); 5.20(s, 1Holef.); 5.42(s, 1Holef.); 7.48 (d, 2Harom., J=9 Hz); 8.00(d, 2Harom., J=9 Hz).