Ethyl Acetate → 4-(Bis(benzyloxy)phosphoryloxy)benzoic acid silver salt

HRID 2100368Notes

Reaction equation

HRID 2100368 reaction equation
[CH2:1]([O:8][P:9]([O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[N+]([O-])([O-])=O.[Ag+:35].CCOC(C)=O>C1COCC1.O>[Ag+:35].[CH2:12]([O:11][P:9]([O:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O-:26])=[O:25])=[CH:27][CH:28]=1)([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 24470Silver NitrateHCID 185411174-(Bis(benzyloxy)phosphoryloxy)benzoic acid

Product 1

HCID 876365924-(Bis(benzyloxy)phosphoryloxy)benzoic acid silver saltYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

4-(bis(benzyloxy)phosphoryloxy)benzoic acid (0.940 g, 2.36 mmol) was dissolved in THF (1.5 mL) and then diluted with water (50 mL). To the resulting suspension was added 1.000 N NaOH solution (2.30 mL, 2.30 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min before a solution of silver nitrate (0.421 g, 2.48 mmol) in water (4 mL) was added over 5 min. Precipitate formed during the addition. The heterogeneous mixture was stirred at rt for 45 min before AcOEt (30 mL) was poured. The whole was stirred at rt for 10 min. The title compound (1.05 g, 88% yield) was collected as a white solid by suction filtration and dried over Drierite® under vacuum.

Workup

  1. additionwas added over 5 min
  2. customPrecipitate formed during the addition
  3. additionwas poured

Sources & evidence

ORD record
ord-ddf8f231f96e42ed851c6b84317a157f
Source dataset
uspto-grants-2009_08
Patent number
US07572795B2

Reaction notes

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