Sodium Hydroxide → 3-Benzo[1,3]dioxol-5-yl-5-benzyloxy-benzoic Acid

HRID 1670075Notes

Reaction equation

HRID 1670075 reaction equation
C[O:2][C:3](=[O:27])[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]([C:18]2[CH:26]=[CH:25][C:21]3[O:22][CH2:23][O:24][C:20]=3[CH:19]=2)[CH:5]=1.[OH-].[Na+]>O1CCOCC1>[O:22]1[C:21]2[CH:25]=[CH:26][C:18]([C:6]3[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH2:11][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:7]=3)[C:3]([OH:27])=[O:2])=[CH:19][C:20]=2[O:24][CH2:23]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 579059323-Benzo[1,3]dioxol-5-yl-5-benzyloxy-benzoic Acid Methyl Ester

Product 1

HCID 579058343-Benzo[1,3]dioxol-5-yl-5-benzyloxy-benzoic AcidYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Benzo[1,3]dioxol-5-yl-5-benzyloxy-benzoic acid methyl ester (14.2 g) was dissolved in 1,4-dioxane (200 mL) and then 1 M aq. NaOH (40 mL) was added. The mixture was stirred at room temperature overnight. The solvents were removed under reduced pressure and the residue was diluted with water (200 mL). It was then made acidic by addition of 10% HCl (aq.) solution and the precipitated material was collected by filtration. The solid was washed with water and dried to yield 13.2 g (97% yield) of the title compound.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionthe residue was diluted with water (200 mL)
  3. additionmade acidic by addition of 10% HCl (aq.) solution
  4. filtrationthe precipitated material was collected by filtration
  5. washThe solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-98aa8d1dc14548ef902dbda8b628317c
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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