Potassium Hydroxide → HCID 15913970, compound

HRID 1977514Notes

Reaction equation

HRID 1977514 reaction equation
C([O:3][C:4](=[O:40])[CH:5]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:6][CH2:7][CH:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]([O:11]CC)=[O:10])C.[OH-].[K+]>O.CO>[C:34]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH2:27][CH:5]([CH2:6][CH2:7][CH:8]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]([OH:11])=[O:10])[C:4]([OH:40])=[O:3])[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15913969HCID 15913969, compound

Product 1

HCID 15913970HCID 15913970, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To the 2,5-bis(2-phenyl-benzyl) adipic acid diethylester, obtained as described above, were added 180 mL of a solution of 6M KOH in H2O/MeOH and the reaction mixture was refluxed for 16 hours. MeOH was removed on a rotary evaporator and the aqueous layer was washed with Et2O (2×200 mL). The alkaline aqueous layer was acidified, at 0° C., with HCl 37% to pH 1. A white/yellow powder was formed, filtered off and washed with water and a little hexane. Said powder was thoroughly dried, to afford 77.0 g of 2,5-bis(2-phenyl-benzyl) adipic acid (85% yield).

Workup

  1. temperaturethe reaction mixture was refluxed for 16 hours
  2. customMeOH was removed on a rotary evaporator
  3. washthe aqueous layer was washed with Et2O (2×200 mL)
  4. customwas acidified, at 0° C., with HCl 37% to pH 1
  5. customA white/yellow powder was formed
  6. filtrationfiltered off
  7. washwashed with water
  8. customwas thoroughly dried

Sources & evidence

ORD record
ord-bd83994d201c480e86a05313e57af424
Source dataset
uspto-grants-2001_05
Patent number
US06232484B1

Reaction notes

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