1-Naphthaldehyde → 2,2-Dimethyl-1-(1-naphthyl)-1,3-propanediol
Reaction equation
[C:1]1([CH:11]=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-:13].[K+]>C(O)C>[CH3:2][C:1]([CH3:11])([CH2:10][OH:13])[CH:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[OH:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-Naphthoaldehyde (57.72 g, 0.37 mol) and isobutylaldehyde (55.0 g, 0.76 mol) was mixed and 85% potassium hydroxide (24.5 g, 0.37 mol) dissolved in ethanol (340 ml) was added dropwise thereto with stirring. Exothermic reaction started immediately, and the temperature reached to 65° C. and then decreased. After dropping for about 15 min, the mixture was stirred at 55° C. for 4.5 hr. The reaction solution was concentrated, and water (300 ml) was added thereto. The mixture was extracted with chloroform (200 ml) twice. The extract was washed with saturated brine, dehydrated with anhydrous sodium sulfate and concentrated to give the title compound as a brown oil (83.62 g, yield 98.1%).