Water → HCID 178501163, compound

HRID 1797006Notes

Reaction equation

HRID 1797006 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([O:13]C)=[O:12])[CH2:7][CH2:6]1)=[O:4].[OH-].[K+].O>CO>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 178501164HCID 178501164, compound

Product 1

HCID 178501163HCID 178501163, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

trans-Cyclohexane-1,4-dicarboxylic acid dimethyl ester (34.2 g, 0.171 mol) was dissolved in 400 mL of anhydrous methanol and the solution brought to reflux. Slowly (dropwise), a solution of KOH (11.2 g, 0.171 mol, 85% purity) in dry methanol was added to the refluxing solution. The solution continued to reflux for 5 hours, and was then cooled and concentrated under reduced pressure to give a white solid. Water was added to dissolve most of the solid, and the aqueous mixture was washed with ether (3×) in a separatory funnel. The aqueous layer was brought to pH ˜6, the resulting white precipitate was collected via filtration and washed (1×) with a small amount of water. Air drying afforded trans-cyclohexane-1,4-dicarboxylic acid monomethyl ester as a white solid.

Workup

  1. temperatureto reflux
  2. temperatureto reflux for 5 hours
  3. temperaturewas then cooled
  4. concentrationconcentrated under reduced pressure
  5. customto give a white solid
  6. dissolutionto dissolve most of the solid
  7. washthe aqueous mixture was washed with ether (3×) in a separatory funnel
  8. filtrationthe resulting white precipitate was collected via filtration
  9. washwashed (1×) with a small amount of water
  10. customAir drying

Sources & evidence

ORD record
ord-1276cca639d64e1fba81804793db0f33
Source dataset
uspto-grants-2006_04
Patent number
US07034034B2

Reaction notes

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