1,3-Bis(benzyloxy)propan-2-ol → 1,3-Bis(benzyloxy)propan-2-one

Temperature

22.5 °C

A mixture of sodium hypochlorite (100 ml, 13% w/v) and saturated sodium bicarbonate (25 ml) was added in one charge to a stirred solution of 1,3-dibenzyloxy-2-propanol (10 g) and 2,2,6,6-tetramethyl-1-piperidinyloxy free radical, (TEMPO) (0.3 g) in toluene (40 ml). The biphasic mixture was stirred at 20-25° C. for 15 minutes when HPLC analysis showed reaction to be complete. The reaction mixture was stirred for a total of 25 minutes at 23° C. The reaction mixture was separated and the organic extract was washed with 5% w/v sodium thiosulfate solution (40 ml) and separated. The organic extract was washed with 1% w/v sodium chloride solution (2×25 ml). The organic extract was then concentrated in vacuo to give an oil which crystallised on standing to give 8.8 g of 1,3-dibenzyloxy-2-propanone in 88.7% yield. The NMR spectrum of the product was concordant with a reference sample.

1. additionwas added in one
2. customreaction
3. stirringThe reaction mixture was stirred for a total of 25 minutes at 23° C
4. customThe reaction mixture was separated
5. extractionthe organic extract
6. washwas washed with 5% w/v sodium thiosulfate solution (40 ml)
7. customseparated
8. extractionThe organic extract
9. washwas washed with 1% w/v sodium chloride solution (2×25 ml)
10. extractionThe organic extract
11. concentrationwas then concentrated in vacuo
12. customto give an oil which
13. customcrystallised

ORD record

ord-8f19164f362840a794041548825df138

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947727B2