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

HRID 1106822Notes

Reaction equation

HRID 1106822 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 (1N, 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-581680b4e7f0436481810f21afdf5f05
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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