Water → 2-Chloro-5,5-dimethyl-4-(1-naphthyl)-1,3,2-dioxaphosphorinane 2-oxide

Temperature

3 °C

2,2-Dimethyl-1-(1-naphthyl)-1,3-propanediol (83.6 g, 0.363 mol) and triethylamine (103.0 g, 1.018 mol) were dissolved in dichloromethane (300 ml). Phosphorus oxychloride (55.4 g, 0.361 mol) dissolved in dichloromethane (80 ml) was added dropwise to the solution above under cooling (2 to 4° C.) and with stirring for 1.5 hr. The solution was stirred at the same temperature for 1 hr, and water (150 ml) was added thereto to partition. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the obtained dark brown oil was added diethylether (100 ml) and diisopropylether (100 ml) and the mixture was stirred thoroughly and then ice-cooled for 1 hr. The upper layer containing a large amount of unreacted 1-naphthoaldehyde was removed by decantation and the under layer was concentrated to give the title compound as a black tar (76.1 g, yield 67.8%).

1. additionwas added dropwise to the solution above
2. stirringThe solution was stirred at the same temperature for 1 hr
3. customto partition
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. additionTo the obtained dark brown oil was added diethylether (100 ml) and diisopropylether (100 ml)
8. stirringthe mixture was stirred thoroughly
9. temperatureice-cooled for 1 hr
10. additionThe upper layer containing a large amount of unreacted 1-naphthoaldehyde
11. customwas removed by decantation
12. concentrationthe under layer was concentrated

ORD record

ord-81dbfd241d4e46868c0775e50647a9c5

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07420070B2