Benzaldehyde → 1-Phenyl-1-propanol

To a Schlenk flask containing degassed dry dichloromethane (10 mL) was added the polymer of Example 2 (28.6 mg, 0.1 mmol based on the biphenyl subunit) and diethylzinc (0.42 mL, 4 mmol). The resulting mixture was stirred at r.t. for 2.5 h. Benzaldehyde (0.2 mL, 2 mmol) was then added and the reaction mixture was stirred at r.t. for 112 h. Water (5 mL) and 1N HCl (5 mL) were added to quench the reaction. The polymer catalyst was filtered off and recovered. The organic layer in the filtrate was separated and the aqueous layer was extracted with dichloromethane. The combined organic phase was dried over Na2SO4 and concentrated under reduced pressure. 1H NMR spectroscopic analysis of this crude product indicated a complete conversion and the ratio of 1-phenyl-1-propanol to benzyl alcohol (a side product) was 53:47. Column chromatography on silica gel (eluent: EtOAc/hexanes=1/4) gave 1-phenyl-1-propanol as a colorless liquid (117 mg, 43%). GC analysis on a chiral column (β-Dex capillary column, Supelco Company) showed an ee of 13%.

1. additionTo a Schlenk flask containing
2. customdegassed dry dichloromethane (10 mL)
3. additionwas added the polymer of Example 2 (28.6 mg, 0.1 mmol
4. stirringthe reaction mixture was stirred at r.t. for 112 h
5. customto quench
6. customthe reaction
7. filtrationThe polymer catalyst was filtered off
8. customrecovered
9. customThe organic layer in the filtrate was separated
10. extractionthe aqueous layer was extracted with dichloromethane
11. dry with materialThe combined organic phase was dried over Na2SO4
12. concentrationconcentrated under reduced pressure

ORD record

ord-55a0b4fc443641919c8d402ca23a8c72

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05889134