1-Butanol → Di-n-butyl cis-1,3-Cyclohexanedicarboxylate

HRID 321911Notes

Reaction equation

HRID 321911 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][CH2:14][CH3:15].[C:17]1(C)C=C[CH:20]=[CH:19][CH:18]=1.C1(C)C=CC(S(O)(=O)=[O:31])=CC=1>O>[C@H:3]1([C:7]([O:8][CH2:17][CH2:18][CH2:19][CH3:20])=[O:31])[CH2:4][CH2:5][CH2:6][C@@H:1]([C:10]([O:9][CH2:12][CH2:13][CH2:14][CH3:15])=[O:11])[CH2:2]1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 11367118cis-1,3-Cyclohexanedicarboxylic anhydride

Product 1

HCID 21967256Di-n-butyl cis-1,3-Cyclohexanedicarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Anhydride 1 (3.85 g; 25 mmol) was combined with n-butanol (11.4 mL; 125 mmol; 5 equiv) and toluene (25 mL). 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 2.5 h at reflux, GC analysis indicated no residual 1. The reaction mixture was washed with saturated aqueous sodium bicarbonate (5 mL).

Workup

  1. temperaturethe reaction mixture was heated
  2. distillationcould be continuously distilled
  3. temperatureAfter 2.5 h at reflux
  4. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate (5 mL)

Sources & evidence

ORD record
ord-6af23158ba5b48f1a32a46fae7cb20ac
Source dataset
uspto-grants-2001_04
Patent number
US06210956B1

Reaction notes

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