Citric Acid → HCID 18510786, compound

HRID 1370541Notes

Reaction equation

HRID 1370541 reaction equation
[CH:1]1(N)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:10](CC)CC)C.[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1>[CH:1]1([C:17]23[CH:21]=[CH:22][CH:23]=[CH:24][CH:16]2[C:15]([NH:10][C:18]3=[O:19])=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6811Phthalic AnhydrideHCID 7965CyclohexylamineHCID 8471Triethylamine

Product 1

HCID 18510786HCID 18510786, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Cyclohexylamine (50.20 ml, 0.44 mol) and triethylamine (51.76 ml, 0.37 mol) were added to a suspension of phthalic anhydride (50.00 g, 0.34 mol) in toluene (500 ml) at room temperature. The mixture was stirred at 110° C. overnight. The temperature of the system was then returned to room temperature, and a 0.1 N aqueous citric acid solution was added thereto. The mixture was extracted with ethyl acetate. The extract was washed with saturated saline and dried over anhydrous MgSO4. The solvent was then removed by distillation under the reduced pressure. The precipitated crystals were collected by suction filtration, washed with hexane, and then dried to give 55.28 g (71%) of 2-cyclohexylphthalimide as a white crystalline product.

Workup

  1. customwas then returned to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated saline
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was then removed by distillation under the reduced pressure
  6. filtrationThe precipitated crystals were collected by suction filtration
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-cca992439c9c40e0ace318cf402a3b30
Source dataset
uspto-grants-2003_06
Patent number
US06583144B2

Reaction notes

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