Hydrochloric Acid → 4-(1-Formyl-heptyl)-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[CH:17][O:18]C)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=1.Cl>O1CCCC1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:17]=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-(1-Methoxymethylene-heptyl)-benzoic acid methyl ester (3.5 g, 12.68 mmol) is dissolved in tetrahydrofuran (50 mL) and concentrated hydrochloric acid (5 mL) is added. The system is purged of air with nitrogen and heated to reflux for 6 h. The reaction is monitored by HPLC. The reaction is allowed to cool to room temperature and then neutralized with 30% potassium hydroxide solution and bicarbonate. The two phases are separated and the aqueous extracted a second time with diethyl ether. The combined organic extracts are washed with brine, dried over sodium sulfate, and concentrated. The crude material is loaded onto a silica gel column and purified using hexanes/ethyl acetate. MS (ES): 261.2 [M+H]−.