Heptane → 1,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acid

HRID 1484011Notes

Reaction equation

HRID 1484011 reaction equation
[C:1]([O:9][CH3:10])(=[O:8])/[CH:2]=[CH:3]/[C:4]([O:6][CH3:7])=[O:5].[C:11]([OH:24])(=[O:23])[C:12]1([CH2:22][CH2:21][CH:17]([C:18]([OH:20])=[O:19])[C:14]1([CH3:16])[CH3:15])[CH3:13].CCCCCCC>C(OCC)(=O)C>[C:1]([O:9][CH3:10])(=[O:8])/[CH:2]=[CH:3]/[C:4]([O:6][CH3:7])=[O:5].[C:11]([OH:24])(=[O:23])[C:12]1([CH2:22][CH2:21][CH:17]([C:18]([OH:20])=[O:19])[C:14]1([CH3:16])[CH3:15])[CH3:13].[C:1]([O:9][CH3:10])(=[O:8])/[CH:2]=[CH:3]/[C:4]([O:6][CH3:7])=[O:5].[C:11]([OH:24])(=[O:23])[C:12]1([CH2:22][CH2:21][CH:17]([C:18]([OH:20])=[O:19])[C:14]1([CH3:16])[CH3:15])[CH3:13]

Participants

7

Reactant 3

HCID 8900HeptaneHCID 214911,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acid3×HCID 637568Dimethyl Fumarate3×

Product 3

HCID 214911,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acidHCID 637568Dimethyl FumarateHCID 117762171Dimethyl fumarate (+)-camphoric acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateCatalyst

Procedure

Cocrystals of dimethyl fumarate and (+)-camphoric acid were prepared as follows. 36 mg of dimethyl fumarate and 200 mg of (+)-camphoric acid were combined in an agate jar with a 4 ml capacity. One drop of 1:3 (v:v) ethyl acetate:heptane was added along with two agate grinding balls. The mixture was milled for 60 minutes at full power on a Retch mm2 mixer mill. The starting concentrations of dimethyl fumarate and (+)-camphoric acid were chosen such that the thermodynamically stable solid phase at equilibrium is the cocrystal of dimethyl fumarate and (+)-camphoric acid. The crystalline material that formed was isolated to yield the dimethyl fumarate: (+)-camphoric acid (1:4, by NMR) cocrystal. The measured melting points were 103±1° C. for dimethyl fumarate, 185±2° C. for (+)-camphoric acid, and 88±2° C. for the cocrystal.

Workup

  1. customgrinding balls
  2. customThe mixture was milled for 60 minutes at full power on a Retch mm2 mixer mill
  3. customThe crystalline material that formed
  4. customwas isolated

Sources & evidence

ORD record
ord-fb529b7458ef44eb88ef917936aaa5a0
Source dataset
uspto-grants-2016_08
Patent number
US09421182B2

Reaction notes

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