Curcumin → Curcumin bis-methylsuccinate

HRID 1675388Notes

Reaction equation

HRID 1675388 reaction equation
[CH3:1][O:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5](/[CH:10]=[CH:11]/[C:12]([CH2:14][C:15](/[CH:17]=[CH:18]/[C:19]2[CH:27]=[C:24]([O:25][CH3:26])[C:22]([OH:23])=[CH:21][CH:20]=2)=[O:16])=[O:13])[CH:4]=1.[Cl-].[CH3:29][O:30][C:31](=[O:37])[CH2:32][CH2:33][C:34]([OH:36])=[O:35]>O1CCCC1.N1C=CC=CC=1.C1(C)C=CC=CC=1.C(OC(=O)C)C>[CH3:26][O:25][C:24]1[C:22]([OH:23])=[CH:21][CH:20]=[C:19](/[CH:18]=[CH:17]/[C:15]([CH2:14][C:12](/[CH:11]=[CH:10]/[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([OH:9])=[CH:7][CH:6]=2)=[O:13])=[O:16])[CH:27]=1.[CH3:29][O:30][C:31](=[O:37])[CH2:32][CH2:33][C:34]([O:36][CH3:1])=[O:35]

Participants

7

Reactant 2

HCID 969516CurcuminHCID 86605420Succinic acid methylester chloride

Product 1

HCID 86637943Curcumin bis-methylsuccinateYield 171%

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.68 g curcumin (10 mmole) in 20 ml tetrahydrofuran and 3 ml pyridine was slowly added at 0° C. a solution of 2.83 ml succinic acid monomethylesterchloride (23 mmole) in 5 ml of toluene. After stirring for 24 h at ambient, the reaction mixture was diluted with 100 ml acetic acid ethylester and washed with water. The organic phase was evaporated and the residue crystallised from ethyl acetate to yield 4.4 g curcumin-bis-methylsuccinate, m.p. 145-147° C.

Workup

  1. washwashed with water
  2. customThe organic phase was evaporated
  3. customthe residue crystallised from ethyl acetate

Sources & evidence

ORD record
ord-62dcfeec62f84878a4ba266b7786310f
Source dataset
uspto-grants-2011_08
Patent number
US08003686B2

Reaction notes

Loading…