Succinic anhydride → Matairesinol Succinate

HRID 490784Notes

Reaction equation

HRID 490784 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]2[C@@H:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([O:24][CH3:25])[CH:23]=3)[C:14](=[O:15])[O:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[OH:9].[C:27]1(=[O:33])[O:32][C:30](=[O:31])[CH2:29][CH2:28]1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]2[C@@H:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([O:24][CH3:25])[CH:23]=3)[C:14](=[O:15])[O:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[OH:9].[C:27]([O-:32])(=[O:33])[CH2:28][CH2:29][C:30]([O-:2])=[O:31]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 119205(-)-Matairesinol

Product 1

HCID 86597911Matairesinol Succinate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Matairesinol (500 mg, 1.4 mmol) was dissolved in 30 ml pyridine. To the solution succinic anhydride (700 mg, 7 mmol) was added in small portions. The temperature was adjusted to 50° C. and the mixture was stirred for 24 h. The solvent was removed under reduced-pressure and the residue dissolved in dichloromethane and extracted first with slightly basic water. The water phase was then acidified with 10% HCl and extracted with dichloromethane. The organic phases were combined, concentrated and chromatographed on a silica column using CHCl3:EtOAc (1:1) as eluent. The fractions containing the product were combined and the solvents were removed.

Workup

  1. customwas adjusted to 50° C.
  2. customThe solvent was removed under reduced-pressure
  3. dissolutionthe residue dissolved in dichloromethane
  4. extractionextracted first with slightly basic water
  5. extractionextracted with dichloromethane
  6. concentrationconcentrated
  7. customchromatographed on a silica column
  8. additionThe fractions containing the product
  9. customthe solvents were removed

Sources & evidence

ORD record
ord-10c54edacbaa4701b4ec6d92fc20c9de
Source dataset
uspto-grants-2009_05
Patent number
US07528166B2

Reaction notes

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