p-Toluenesulfonic acid → HCID 10977233, compound

HRID 321908

Reaction equation

HRID 321908 reaction equation
[C@H:1]12[C:10](=O)[O:9][C:7](=[O:8])[C@H:3]([CH2:4][CH2:5][CH2:6]1)[CH2:2]2.[CH:12]([O:19]CC)([O:16][CH2:17][CH3:18])OCC.[C:22]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[C@H:5]1([C:12]([O:16][CH2:17][CH3:18])=[O:19])[CH2:6][CH2:1][CH2:2][C@@H:3]([C:7]([O:9][CH2:10][CH3:22])=[O:8])[CH2:4]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 11367118cis-1,3-Cyclohexanedicarboxylic anhydride

Product 1

HCID 10977233HCID 10977233, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Anhydride 1 (7.71 g; 50 mmol) was combined with triethyl orthoformate (12.5 mL; 75 mmol; 1.5 equiv) and ethanol (50 mL). p-Toluenesulfonic acid (0.48 g; 2.5 mmol; 0.05 equiv) was added and the reaction mixture was heated overnight at 60° C. to completely consume 1. Solid sodium bicarbonate (0.5 g) was added and the solvent was removed at reduced pressure. The residue was dissolved in toluene (25 mL), washed with saturated aqueous NaHCO3 (5 mL), dried over Na2SO4, and concentrated to afford 11.42 g (99%) of cis-2b which was a single peak by GC analysis.

Workup

  1. customto completely consume 1
  2. additionSolid sodium bicarbonate (0.5 g) was added
  3. customthe solvent was removed at reduced pressure
  4. dissolutionThe residue was dissolved in toluene (25 mL)
  5. washwashed with saturated aqueous NaHCO3 (5 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto afford 11.42 g (99%) of cis-2b which

Sources & evidence

ORD record
ord-103a8571befd42b9b33d9e2537247ea4
Source dataset
uspto-grants-2001_04
Patent number
US06210956B1

Linked notes

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