Sodium Hydroxide → 4-(2-(Benzyloxy)benzyloxy)benzoic Acid

HRID 1006025Notes

Reaction equation

HRID 1006025 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][CH:24]=[CH:23][C:10]=1[CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][CH:24]=[CH:23][C:10]=1[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22675491Methyl 4-(2-(benzyloxy)benzyloxy)benzoate

Product 1

HCID 226755644-(2-(Benzyloxy)benzyloxy)benzoic AcidYield 140.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(2-(benzyloxy)benzyloxy)benzoate (1.01 g, 1.91 mmol) was dissolved in THF (20 ml) and methanol (7 ml). The solution was treated with NaOH (IN, 6 ml). The reaction was heated at reflux for 3 hours and then concentrated at reduced pressure. The pH was adjusted to pH1 with concentrated HCl and the solid filtered, washed with water and dried to give the title compound as a white solid (0.9 g, 98%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated at reduced pressure
  4. filtrationthe solid filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-9e2a5cb5293744c5925fbeba2720ff6f
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

Loading…