Ethyl Acetate → HCID 12859206, compound

To a solution of 2-phenylpropane-1,2-diol (3 g, 19.7 mmol) in DCM (60 mL) was added Dess-Martin periodinane (8.36 g, 19.7 mmol) at 0° C. The reaction mixture was stirred for 2 hours at ambient temperature. After completion of the reaction (monitored by TLC (TLC eluent: 30% EtOAc in petroleum ether)), the reaction mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc. The organic layers were combined and washed with water, washed with saturated NaCl solution, and dried on anhydrous Na2SO4. The organic layer was then filtered and concentrated under vacuum to yield intermediate 2-hydroxy-2-phenylpropanal (2 g unpurified) as a colorless liquid. The intermediate thus obtained was used in the next step without any further purification. 1H NMR (400 MHz, CDCl3): δ 9.50 (s, 1H). The 1H NMR spectrum was not completely clean, but since the aldehyde peak at 9.50 ppm was observed, this intermediate was used in the next step without purification.

1. customthe reaction mixture was quenched with saturated NaHCO3 solution
2. extractionextracted with EtOAc
3. washwashed with water
4. washwashed with saturated NaCl solution
5. dry with materialdried on anhydrous Na2SO4
6. filtrationThe organic layer was then filtered
7. concentrationconcentrated under vacuum

ORD record

ord-ecc94d2e71504a76b50b0e9ecd1c4353

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09340549B2