Sulfuric Acid → (4S)-4-hydroxy-2-nonynal

Reaction equation

C([O:3][CH:4](OCC)[C:5]#[C:6][C@@H:7]([O:13]C1CCCCO1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])C.O1CCCC1.S(=O)(=O)(O)O>O>[OH:13][C@@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:6]#[C:5][CH:4]=[O:3]

Participants

Procedure

A mixture of (4S)-1,1-diethoxy-4-(2-tetrahydropyranyloxy)-2-nonyne (96.0 g., 0.31 mole), tetrahydrofuran (500 ml.), and 30% aqueous sulfuric acid (100 ml.) is stirred at room temperature for 17 hours. The solution is diluted with water and the oily product is extracted with ether. The ether extract is washed with sodium bicarbonate solution and water and dried over sodium sulfate. Evaporation of the ether leaves (4S)-4-hydroxy-2-nonynal as a colorless residual oil which is used in the following step without further purification.