Sodium Hydroxide → 2-Benzyloxy-benzene-1,3,5-tricarboxylic acid

HRID 1038288Notes

Reaction equation

HRID 1038288 reaction equation
C([O:8][C:9]([C:11]1[CH:16]=[C:15]([C:17]([O:19]CC2C=CC=CC=2)=[O:18])[CH:14]=[C:13]([C:27]([O:29]CC2C=CC=CC=2)=[O:28])[C:12]=1[O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:10])C1C=CC=CC=1.[OH-].[Na+]>CO.O>[CH2:38]([O:37][C:12]1[C:11]([C:9]([OH:10])=[O:8])=[CH:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][C:13]=1[C:27]([OH:29])=[O:28])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57572477HCID 57572477, compound

Product 1

HCID 575724722-Benzyloxy-benzene-1,3,5-tricarboxylic acid

Reagents, catalysts & solvents 1

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

Procedure

2-Benzyloxy-benzene-1,3,5-tricarboxylic acid tribenzyl ester (14) (52 g, 88 mmol) was hydrolyzed with NaOH (20 g, 0.5 mol) in 4:1 methanol-water (1 L). The solvents were removed under reduced pressure after the completion of hydrolysis, and the residue was dissolved in saline and extracted with recycling methylene chloride to remove the benzyl alcohol. 2-benzyloxy benzene-1,3,5-tricarboxylic acid (15) deposited after acidification of the solution. It was collected by filtration and dried under vacuum, yield 25.6 g, 92%.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customafter the completion of hydrolysis
  3. dissolutionthe residue was dissolved in saline
  4. extractionextracted with recycling methylene chloride
  5. customto remove the benzyl alcohol
  6. filtrationIt was collected by filtration
  7. customdried under vacuum, yield 25.6 g, 92%

Sources & evidence

ORD record
ord-ee2d0018358c4418ba7b034d533259db
Source dataset
uspto-grants-2013_10
Patent number
US08551453B2

Reaction notes

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