Water → Di-n-propyl cis-1,3-cyclohexanedicarboxylate

HRID 321909Notes

Reaction equation

HRID 321909 reaction equation
[C@H:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C@H:3]([CH2:4][CH2:5][CH2:6]1)[CH2:2]2.[CH2:12](O)[CH2:13][CH3:14].[C:16]1(C)[CH:21]=CC(S(O)(=O)=O)=C[CH:17]=1.[OH2:27]>C1(C)C=CC=CC=1>[C@H:3]1([C:7]([O:8][CH2:17][CH2:16][CH3:21])=[O:27])[CH2:4][CH2:5][CH2:6][C@@H:1]([C:10]([O:9][CH2:12][CH2:13][CH3:14])=[O:11])[CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 10311-PropanolHCID 6101p-Toluenesulfonic acidHCID 11367118cis-1,3-Cyclohexanedicarboxylic anhydride

Product 1

HCID 21967257Di-n-propyl cis-1,3-cyclohexanedicarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Anhydride 1 (3.85 g; 25 mmol) was dissolved in toluene (25 mL) and n-propanol (9.3 mL; 125 mmol; 5 equiv). p-Toluenesulfonic acid (238 mg; 1.25 mmol; 0.05 equiv) was added and the reaction mixture was heated to reflux under conditions where water could be continuously distilled using a Dean-Stark trap. After 2 h at reflux, GC analysis indicated no residual 1. The reaction mixture was washed with saturated aqueous sodium bicarbonate (5 mL). The organic solution was dried over MgSO4 and concentrated to afford 6.24 g (97%) of cis-2c which was a single peak by GC analysis.

Workup

  1. temperaturethe reaction mixture was heated
  2. distillationcould be continuously distilled
  3. temperatureAfter 2 h at reflux
  4. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate (5 mL)
  5. dry with materialThe organic solution was dried over MgSO4
  6. concentrationconcentrated
  7. customto afford 6.24 g (97%) of cis-2c which

Sources & evidence

ORD record
ord-061e508939a0479bb566da6d597c7145
Source dataset
uspto-grants-2001_04
Patent number
US06210956B1

Reaction notes

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