Potassium Permanganate → 4-(Bis(benzyloxy)phosphoryloxy)benzoic acid

HRID 2100367

Reaction equation

HRID 2100367 reaction equation
[P:1]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][CH:21]=1)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[Mn]([O-])(=O)(=O)=[O:29].[K+].OS([O-])=O.[Na+].CO.C(Cl)Cl>CC(C)=O.O.Cl>[CH2:4]([O:3][P:1]([O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([OH:29])=[O:27])=[CH:24][CH:25]=1)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 516875Potassium PermanganateHCID 21226129Dichloromethane methanolHCID 23665763Sodium BisulfiteHCID 57798977Dibenzyl 4-formylphenyl phosphate

Product 1

HCID 185411174-(Bis(benzyloxy)phosphoryloxy)benzoic acidYield 90.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of dibenzyl 4-formylphenyl phosphate (1.00 g, 2.62 mmol) in acetone (50 mL) was added a solution of potassium permanganate (0.837 g, 5.30 mmol) in acetone (40 mL) and water (40 mL) at rt over 1.5 hr. To the resulting purple mixture was poured 10% NaHSO3 in 1N HCl (100 mL) at rt. The purple solution became colorless and extracted with AcOEt (3×60 mL). The combined extract was washed with brine and dried anhydrous MgSO4. The title compound (0.940 g, 90% yield) was isolated as a white solid by ISCO (5% MeOH/CH2Cl2).

Workup

  1. extractionextracted with AcOEt (3×60 mL)
  2. extractionThe combined extract
  3. washwas washed with brine and dried anhydrous MgSO4

Sources & evidence

ORD record
ord-085d8233d79e480e87e7c8948c45fc50
Source dataset
uspto-grants-2009_08
Patent number
US07572795B2

Linked notes

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