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

HRID 355784
Notes
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Reaction equation

HRID 355784 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-7486a844c27f4d83bd0bf51e8ed95ae2
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05834468

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes