Methanol → Dimethyl cyclohexane-1,3-dicarboxylate

HRID 1408852Notes

Reaction equation

HRID 1408852 reaction equation
[CH:1]1([C:10]([OH:12])=[O:11])[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([OH:9])=O)[CH2:2]1.Cl[Si](C)(C)[CH3:15].[CH3:18][OH:19]>C1COCC1>[CH3:18][O:19][C:7]([CH:3]1[CH2:4][CH2:5][CH2:6][CH:1]([C:10]([O:12][CH3:15])=[O:11])[CH2:2]1)=[O:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 1072051,3-Cyclohexanedicarboxylic acid

Product 1

HCID 138896Dimethyl cyclohexane-1,3-dicarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,3-Cyclohexanedicarboxylic acid (45.0 g, 261.4 mmol) was dissolved in methanol (250 mL). Chlorotrimethylsilane (10.00 mL, 78.79 mmol) was added and the reaction was stirred at room temperature for 4 days. The reaction was checked by LC-MS with the product mass [M+H]+ 201 seen. The mixture was concentrated under reduced pressure. The resulting residue was diluted with dichloromethane (200 mL). The organic layer was then washed with saturated. NaHCO3, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a slightly viscous, clear and colorless oil. The oil was redissolved in anhydrous THF and concentrated to yield 49.5 g (95%) of cyclohexane-1,3-dicarboxylic acid dimethyl ester, which was used in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionThe resulting residue was diluted with dichloromethane (200 mL)
  3. washThe organic layer was then washed with saturated
  4. dry with materialNaHCO3, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a slightly viscous, clear and colorless oil
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-90eed563e9824f2e9c3ccda02af48886
Source dataset
uspto-grants-2014_12
Patent number
US08921370B2

Reaction notes

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