Water → Methyl 4-oxocyclohexanecarboxylate

HRID 1770117Notes

Reaction equation

HRID 1770117 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5](C(OC)=O)([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH:3]1C(OC)=O.[Cl-].[Na+].O>CN(C=O)C>[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962Water2×HCID 5234Sodium ChlorideHCID 13782253Trimethyl 4-oxocyclohexane-1,1,3-tricarboxylate

Product 1

HCID 226643Methyl 4-oxocyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 55 g (0.2 mole) portion of trimethyl 4-oxocyclohexane-1,1,3-tricarboxylate is dissolved in 240 ml DMF and to this is added 26 g (0.445 mole) of sodium chloride and 16 ml (0.89 mole) of water, under nitrogen. This mixture is heated to reflux and maintained for 48 hours, under nitrogen. The reaction is then stripped to dryness under reduced pressure, the residue added to water and the crude product extracted into dichloromethane (3×100 ml). The combined extracts are dried over MgSO4 and stripped to dryness, giving a yellow oil. This crude product is vacuum-distilled to obtain methyl 4-oxocyclohexane-1-carboxylate (b.p. 82°-108° C. at 1.0 mm Hg) which is used directly in the next step.

Workup

  1. temperatureThis mixture is heated
  2. temperatureto reflux
  3. temperaturemaintained for 48 hours, under nitrogen
  4. extractionthe crude product extracted into dichloromethane (3×100 ml)
  5. dry with materialThe combined extracts are dried over MgSO4
  6. customgiving a yellow oil
  7. distillationThis crude product is vacuum-distilled

Sources & evidence

ORD record
ord-7426b68adff64589bacd10498e0675c5
Source dataset
uspto-grants-1995_01
Patent number
US05385912

Reaction notes

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