Benzyl Alcohol → HCID 178503023, compound

Dichloromethylphosphite (10.0 g, 77 mmol) in 80 mL of dry diethyl ether was cooled to −20° C. under an atmosphere of nitrogen. A solution of benzyl alcohol (23 g, 213 mmol) and triethylamine (10.2 g, 100 mmol) in 40 mL of diethyl ether was added dropwise over 1 hour while maintaining an internal temperature range of 0° C. to 10° C. Once addition was complete the mixture was warmed to room temperature and stirred overnight. The mixture was filtered and the solid cake washed with 200 mL of diethyl ether. The organics were combined and evaporated under reduced pressure to give 25 g of a clear and colorless liquid. The liquid was purified by flash chromatography and eluted with a 1:1 hexane/ethyl acetate to ethyl acetate gradient. The desired fractions were collected and evaporated to give methyl O-benzylphosphinic acid (1, R=CH3, R1=CH2Ph, 6.5 g, 50%) as a clear and colorless oil. Rf 0.1 (1:1, Hexane/EtOAc).

1. temperaturewhile maintaining an internal temperature range of 0° C. to 10° C
2. additionOnce addition
3. filtrationThe mixture was filtered
4. washthe solid cake washed with 200 mL of diethyl ether
5. customevaporated under reduced pressure
6. customto give 25 g of a clear and colorless liquid
7. customThe liquid was purified by flash chromatography
8. washeluted with a 1:1 hexane/ethyl acetate to ethyl acetate gradient
9. customThe desired fractions were collected
10. customevaporated

ORD record

ord-5e14fc9ee3c6464fad58d26ab4ca359c

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06372726B1