Sulfuric Acid → Diethyl 2-carboxybenzylphosphonate

HRID 4916

Reaction equation

HRID 4916 reaction equation
C[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[O-][Mn](=O)(=O)=O.[K+].[C:23]([O-:26])([O-])=[O:24].[Na+].[Na+].OS(O)(=O)=O>O>[C:23]([C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])([OH:26])=[O:24]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 112945Phosphonic acid, P-((2-methylphenyl)methyl)-, diethyl esterHCID 516875Potassium Permanganate

Product 1

HCID 11369294Diethyl 2-carboxybenzylphosphonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4 g of diethyl 2-methylbenzylphosphonate were added to a solution of 12 g of KMnO4 and 4 g of Na2CO3 in 300 ml of water and the mixture was boiled under reflux for 24 hours. It was acidified with 15 ml of concentrated H2SO4 and extracted five times with 300 ml of ether each time. The organic phase was dried over MgSO4, the solvent was evaporated off on a rotary evaporator and the residue was chromatographed over silica gel (CH2Cl2 /methanol/triethylamine 9/1/0.1).

Workup

  1. temperatureunder reflux for 24 hours
  2. extractionextracted five times with 300 ml of ether each time
  3. dry with materialThe organic phase was dried over MgSO4
  4. customthe solvent was evaporated off on a rotary evaporator
  5. customthe residue was chromatographed over silica gel (CH2Cl2 /methanol/triethylamine 9/1/0.1)

Sources & evidence

ORD record
ord-3b1908a01a5143ef967011e4244289b7
Source dataset
uspto-grants-1993_09
Patent number
US05242908

Linked notes

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