p-Toluenesulfonic acid → Dimethyl cis-1,3-cyclohexanedicarboxylate

HRID 377943

Reaction equation

HRID 377943 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:17]C)([O:15][CH3:16])OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C@H:1]1([C:12]([O:15][CH3:16])=[O:17])[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 11367118cis-1,3-Cyclohexanedicarboxylic anhydride

Product 1

HCID 11264108Dimethyl cis-1,3-cyclohexanedicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Anhydride 1 (3.85 g; 25 mmol) was combined with trimethyl orthoformate (4.10 mL; 37.5 mmol; 1.5 equiv) and methanol (8.2 mL). p-Toluenesulfonic acid (238 mg; 1.25 mmol; 0.05 equiv) was added and the reaction mixture was stirred overnight at ambient temperature to completely consume 1 and afford a single product by GC analysis. The solvent was removed at reduced pressure and the residue was dissolved in ethyl acetate (30 mL), washed with saturated aqueous NaHCO3 (10 mL), dried over MgSO4, and concentrated to afford 4.91 g (98%) of cis-2a which gave a single peak by GC analysis.

Workup

  1. customto completely consume 1
  2. customafford a single product by GC analysis
  3. customThe solvent was removed at reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate (30 mL)
  5. washwashed with saturated aqueous NaHCO3 (10 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto afford 4.91 g (98%) of cis-2a which
  9. customgave a single peak by GC analysis

Sources & evidence

ORD record
ord-c4f78c7f979447d3852ed2d9f5025033
Source dataset
uspto-grants-2000_02
Patent number
US06028213

Linked notes

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