Hydrogen Bromide → Tri-O-acetyl-D-glucal

Tri-O-acetyl-D-glucal was synthesized according to the following procedure. Alternatively it could be commercially obtained from Pfanstiehl Laboratories Inc. (Wankeyan, Ill.), however the procedure described below has the advantage of reduced cost compared to the commercial source. Glucose (1.000 g) was suspended in a solution of acetic acid (10 mL) and acetic anhydride (3.606 g, 7.0 equiv) and 1.000 g 31% HBr/acetic acid solution added. The reaction mixture was allowed to stir for 1 h, after which 9.000 g more 31% HBr/acetic acid solution (total of 7.7 equiv HBr) was added and allowed to stir overnight. Sodium acetate was then added (2.700 g) to neutralized the excess HBr, and the reaction mixture was added to a suspension containing pulverized CuSO4:5H2O (0.315 g), zinc (12.600 g), water (10 mL), sodium acetate (9.450 g), and acetic acid (5 mL) and the resultant reaction mixture was stirred vigorously for 1.5 h. The solution was then filtered and the solid washed with ethyl acetate (100 mL) and water (100 mL). The organic layer of the filtrate was then washed with NaHCO3 (100 mL) and brine (50 mL), dried (Na2SO4), filtered and the solvent removed under reduced pressure to provide tri-O-acetyl-D-glucal (1.350 g, 98%) as a colorless oil

1. customTri-O-acetyl-D-glucal was synthesized
2. additionadded
3. stirringto stir overnight
4. additionthe reaction mixture was added to a suspension
5. additioncontaining
6. stirringwas stirred vigorously for 1.5 h
7. filtrationThe solution was then filtered
8. washthe solid washed with ethyl acetate (100 mL) and water (100 mL)
9. washThe organic layer of the filtrate was then washed with NaHCO3 (100 mL) and brine (50 mL)
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. customthe solvent removed under reduced pressure

ORD record

ord-b9ed6bede6d045b8b09db5ab4145fc6d

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517891B2