Nitric Acid → (3R,3aR,6S,6aR)-Hexahydrofuro[3,2-b]furan-3,6-diyl diacetate

HRID 462130

Reaction equation

HRID 462130 reaction equation
[CH2:1]1[O:5][C@@H:4]2[C@@H:6](O)[CH2:7][O:8][C@@H:3]2[C@@H:2]1[OH:10].[C:11]([O:14][C:15](=[O:17])[CH3:16])(=O)[CH3:12].[N+]([O-])(O)=[O:19]>>[CH3:16][C:15]([O:14][C@H:11]1[C@H:1]2[O:5][CH2:4][C@H:3]([O:8][C:7]([CH3:6])=[O:19])[C@H:2]2[O:10][CH2:12]1)=[O:17]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 12597Isosorbide

Product 1

HCID 11770257(3R,3aR,6S,6aR)-Hexahydrofuro[3,2-b]furan-3,6-diyl diacetate

Procedure

Either one of the above residues containing the mixture of the 2-acetate, 5-acetate and 2,5-diacetate of 1,4:3,6-dianhydro-D-glucitol is nitrated. The preferred nitration method is to add slowly the residue over a period of 0.1 to 5 hours to a solution at -5° to 25° C, preferably 0° to 5° C, of one to 20 molar equivalents, preferably three to five molar equivalents, of acetic anhydride and one to ten molar equivalents, preferably one to two molar equivalents, of nitric acid. After the addition is completed, the reaction mixture is stirred for about 0.5 to 2 hours at -5° to 25° C, preferably 0° to 5° C, in order to complete the nitration. In this manner a solution containing a mixture of 1,4:3,6-dianhydro-D-glucitol 5-acetate 2-nitrate, 1,4:3,6-dianhydro-D-glucitol 2-acetate 5-nitrate and 1,4:3,6-dianhydro-D-glucitol 2,5-diacetate is obtained.

Workup

  1. additionEither one of the above residues containing
  2. additionto add slowly the residue over a period of 0.1 to 5 hours to a solution at -5° to 25° C
  3. custompreferably 0° to 5° C
  4. additionAfter the addition
  5. additionIn this manner a solution containing

Sources & evidence

ORD record
ord-c7240821e75f4326b1c3544b08dd135f
Source dataset
uspto-grants-1977_12
Patent number
US04065488

Linked notes

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