Sodium Hydroxide → 3,5-Bis(phenylmethoxy)benzoic acid

HRID 1110289Notes

Reaction equation

HRID 1110289 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[C:6]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=1.[OH-].[Na+]>CO.O1CCOCC1>[C:20]1([CH2:19][O:18][C:6]2[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:7]=2)[C:3]([OH:26])=[O:2])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 2733652Methyl 3,5-bis(benzyloxy)benzoate

Product 1

HCID 993073,5-Bis(phenylmethoxy)benzoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 41.4 g (0.12 mol) of 3,5-bis(phenylmethoxy)benzoic acid methyl ester and 59 ml (0.36 mol) of 6N NaOH in 700 ml of methanol and 350 ml of dioxane was stirred at reflux for 17 hours. The solvents were removed at reduced pressure and the residue was dissolved in water and acidified to pH 3 with 6N HCl. The resultant solid was filtered and recrystallized from methylene chloride-methanol to give 38.6 g (97% yield, mp 211°-213°) of 3,5-bis(phenylmethoxy)benzoic acid.

Workup

  1. temperatureat reflux for 17 hours
  2. customThe solvents were removed at reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe resultant solid was filtered
  5. customrecrystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-7bf8f9f04f154f298691aeae290231fa
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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