2-Naphthalenecarboxaldehyde → 2,2-Dimethyl-1-(2-naphthyl)-1,3-propanediol

2-Naphthoaldehyde (26.0 g, 0.167 mol) and isobutylaldehyde (24.0 g, 0.33 mol) were dissolved in ethanol (50 ml) with heating. 85% Potassium hydroxide (11.0 g, 0.167 mol) dissolved in ethanol (150 ml) was added dropwise to the above solution with stirring. Exothermic reaction started immediately, and the temperature reached to 51° C. and then decreased. After the dropping was completed for about 10 min, the solution was stirred at 55 to 60° C. for 4 hr. The reaction solution was concentrated under reduced pressure, and water (150 ml) was added thereto and the mixture was extracted with chloroform (100 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 (34.86 g, yield 91.0%).

1. temperaturewith heating
2. additionwas added dropwise to the above solution
3. customExothermic reaction
4. customreached to 51° C.
5. stirringthe solution was stirred at 55 to 60° C. for 4 hr
6. concentrationThe reaction solution was concentrated under reduced pressure, and water (150 ml)
7. additionwas added
8. extractionthe mixture was extracted with chloroform (100 ml) twice
9. washThe extract was washed with saturated brine
10. concentrationconcentrated

ORD record

ord-f745ad5278f149238bdb5b3c84685fdd

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07420070B2