Sodium Hydroxide → 3,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzoic acid

HRID 1643696Notes

Reaction equation

HRID 1643696 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:22][CH2:23][O:24][CH3:25])[C:12]=1[CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:8]=[O:9].[OH-:26].[Na+]>CO.O.[N+]([O-])([O-])=O.[Ag+]>[CH3:25][O:24][CH2:23][O:22][C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:12]=1[CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:8]([OH:26])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 866247663,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzaldehyde

Product 1

HCID 667560413,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzoic acidYield 72.1%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 3,5-bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzaldehyde (220f) (42 g, 0.12 mol) in MeOH/H2O (500 mL) was added AgNO3 (21 g, 0.12 mol), followed by NaOH (15 g, 0.36 mol) in one portion at room temperature. The mixture was stirred at room temperature overnight and then filtered. The filtrate was concentrated under vacuum to remove MeOH. The residue was extracted with Et2O (2×100 mL) to remove impurities. The aqueous layer was acidified with conc. HCl to pH 4. The resulting white solid was filtered and dried under vacuum to give the title compound (31 g, 62% yield) as white solid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under vacuum
  3. customto remove MeOH
  4. extractionThe residue was extracted with Et2O (2×100 mL)
  5. customto remove impurities
  6. filtrationThe resulting white solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-9d5d96b9c627411894929cfd51c6f9b5
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

Loading…