Methanol → HCID 18768947, compound

HRID 427413Notes

Reaction equation

HRID 427413 reaction equation
C(OC(=O)[CH:5]([CH2:11][CH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:13]1)[C:6](OCC)=O)C.[OH-:25].[K+].[CH3:27][OH:28]>O>[C:18]1([CH:15]2[CH2:14][CH2:13][CH:12]([CH2:11][CH2:5][CH2:6][C:27]([OH:28])=[O:25])[CH2:17][CH2:16]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 69557395HCID 69557395, compound

Product 1

HCID 18768947HCID 18768947, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

(4-Phenyl-cyclohexylmethyl)-malonic acid diethyl ester (2.79 g, 8.4 mmol, 1.0 equiv) was added to a solution of potassium hydroxide (2.35 g, 41 mmol, 5 equiv) in 20 mL of water and 20 mL of MeOH. The resulting mixture was refluxed for 0.5 h and then evaporated to dryness and then dissolved in 100 mL of water. The solution was washed 3×100 mL with hexane and then brought to pH <1 with concentrated HCl. The product was extracted 3×100 mL EtOAc. The organic layers were combined and concentrated to dryness. The crude product was then heated for 10 min at 180° C. to decarboxylate the diacid and yield the monoacid (0.9 g) which was used without further purification.

Workup

  1. temperatureThe resulting mixture was refluxed for 0.5 h
  2. customevaporated to dryness
  3. dissolutiondissolved in 100 mL of water
  4. washThe solution was washed 3×100 mL with hexane
  5. extractionThe product was extracted 3×100 mL EtOAc
  6. concentrationconcentrated to dryness
  7. customyield the monoacid (0.9 g) which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-8fc6bb75e2594346ae69c5a2abf7208a
Source dataset
uspto-grants-2001_11
Patent number
US06313117B1

Reaction notes

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