HCID 14836344, compound → 4,4-Dipropyl-1,1-cyclohexanediacetic acid

HRID 1088685Notes

Reaction equation

HRID 1088685 reaction equation
[CH2:1]([C:4]1([CH2:21][CH2:22][CH3:23])[CH2:20][CH2:19][C:7]2([CH:12](C#N)[C:11](=[O:15])NC(=O)C2C#N)[CH2:6][CH2:5]1)[CH2:2][CH3:3].Cl.[C:25]([OH:28])(=[O:27])[CH3:26].[OH2:29]>>[CH2:1]([C:4]1([CH2:21][CH2:22][CH3:23])[CH2:20][CH2:19][C:7]([CH2:12][C:11]([OH:29])=[O:15])([CH2:26][C:25]([OH:28])=[O:27])[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 14836344HCID 14836344, compoundHCID 86736801HCID 86736801, compound

Product 1

HCID 148363454,4-Dipropyl-1,1-cyclohexanediacetic acidYield 35%

Procedure

9,9-Dipropyl-1,5 -dicyano-3 -azaspiro[5.5]undecane-2,4 -dione, prepared according to the method of Example 17, was dissolved in a solution of concentrated hydrochloric acid/acetic acid/water (4/7/1) and the solution was heated at reflux for 2 3 days. The reaction mixture was cooled to room temperature and the volatile materials were removed on the rotavap. The residue was partitioned between water and ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated to give the desired acid which was recrystallized from ethyl acetate/hexanes; yield 35-50%.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 2 3 days
  3. customthe volatile materials were removed on the rotavap
  4. customThe residue was partitioned between water and ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fa3ace9247894a36ad107ce92cd10d61
Source dataset
uspto-grants-1990_10
Patent number
US04963557

Reaction notes

Loading…