Hydrochloric Acid → HCID 13585476, compound

HRID 651941Notes

Reaction equation

HRID 651941 reaction equation
[CH2:1]([O:8][P:9]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:22].[K+].Cl.S(=O)(O)[O-].[Na+]>CC(C)=O.O>[CH2:1]([O:8][P:9]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:22])[OH:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516875Potassium PermanganateHCID 13274666HCID 13274666, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13585476HCID 13585476, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 4-phenylbutylphosphonous acid benzyl ester (1.0 gm, 0.0035 moles) in 10 ml acetone and 5 ml water was added a solution of potassium permanganate (0.16 gm, 0.0021 moles) in 5 ml water at 20° C. After the addition (2 minutes), the reaction mixture was stirred at 20° C. for 5 minutes and acidified to pH 1 using concentrated HCl acid. Saturated sodium bisulphite solution was added to the reaction mixture to get a cloudy white solution, which on extraction with ethyl acetate followed by solvent evaporation produced the title compound as a pale yellow oil in 87% (0.92 gm) yield.

Workup

  1. additionAfter the addition (2 minutes)
  2. customto get a cloudy white solution, which
  3. extractionon extraction with ethyl acetate
  4. customfollowed by solvent evaporation

Sources & evidence

ORD record
ord-87f7d7f2a7bc43a18b243fa451357e72
Source dataset
uspto-grants-1987_06
Patent number
US04670193

Reaction notes

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