Acetic Acid → HCID 67295308, compound

HRID 1773851Notes

Reaction equation

HRID 1773851 reaction equation
O=C1N[C:6](=[O:8])[CH:5](C#N)[C:4]2([CH2:15][CH2:14][CH:13]([CH:16]3[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)C1C#N.S(=O)(=O)(O)[OH:28].[C:32]([OH:35])(=[O:34])[CH3:33]>>[C:32]([CH2:33][C:4]1([CH2:5][C:6]([OH:28])=[O:8])[CH2:15][CH2:14][CH:13]([CH:16]2[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]2)[CH2:12][CH2:11]1)([OH:35])=[O:34]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 67294577HCID 67294577, compound

Product 1

HCID 67295308HCID 67295308, compound

Conditions

Temperature
122.5 °C

Procedure

A mixture of 50 g (0.14 mol) of 2,4-dioxo-9-(4-propylcyclohexyl)-3-aza-spiro[5.5]undecane-1,5-dicarbonitrile, 800 ml of glacial acetic acid and 1.51 of 60% sulfuric acid is stirred at 120-125° C. for 5 days. After cooling, the batch is added to ice-water and extracted a number of times with THF/MTBE (1:1). The combined organic phases are washed with saturated sodium chloride solution and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is recrystallised from acetonitrile/THF (2:1), giving (4-carboxymethyl-4′-propylbicyclohexyl-4-yl)acetic acid as a beige solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted a number of times with THF/MTBE (1:1)
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. customdried
  5. concentrationThe solution is concentrated to dryness
  6. customthe residue is recrystallised from acetonitrile/THF (2:1)

Sources & evidence

ORD record
ord-2950ccefa08b4ef1bb083b82bd257c05
Source dataset
uspto-grants-2016_02
Patent number
US09255223B2

Reaction notes

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