Acetic Anhydride → (3R,4R)-3,4-Bis(benzoyloxy)dihydro-2,5-furandione

HRID 388534Notes

Reaction equation

HRID 388534 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]([O:9][C@@H:10]([C:24](O)=[O:25])[C@@H:11]([O:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[C:12]([OH:14])=[O:13])=[O:8])=[CH:3][CH:2]=1.C(OC(=O)C)(=O)C>>[O:25]=[C:24]1[C@H:10]([O:9][C:7](=[O:8])[C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[C@@H:11]([O:15][C:16](=[O:17])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12](=[O:13])[O:14]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 75969Dibenzoyltartaric acid

Product 1

HCID 2733743(3R,4R)-3,4-Bis(benzoyloxy)dihydro-2,5-furandione

Conditions

Temperature
85 °C

Procedure

To a 3-necked, 5 L, round bottom flask fitted with a mechanical stirrer and a Teflon-coated thermocouple was added (−)-2,3-dibenzoyl-L-tartaric acid (1000 g, 2.79 mol) followed by acetic anhydride (2 L). The suspension was stirred and heated to 85° C. for 2 h during which time the starting material gradually dissolved. A short time thereafter, the product began to crystallize in the reaction mixture and the suspension was then cooled to 25° C. The product was collected by filtration, washed with 10% acetone in hexane (2×1 L), and dried in a vacuum oven at 50° C. overnight to afford the title compound (5a) as a white solid. 1H NMR (CDCl3, 400 MHz): δ 6.0 (s, 2H), 7.45 (app. t, 4H), 7.65 (app. t, 2H), 8.05 (d, 4H).

Workup

  1. customTo a 3-necked, 5 L, round bottom flask fitted with a mechanical stirrer
  2. dissolutiongradually dissolved
  3. customto crystallize in the reaction mixture
  4. temperaturethe suspension was then cooled to 25° C
  5. filtrationThe product was collected by filtration
  6. washwashed with 10% acetone in hexane (2×1 L)
  7. customdried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-ca7e109d12e6405bb125a7001f1bd99b
Source dataset
uspto-grants-2013_02
Patent number
US08377956B2

Reaction notes

Loading…