Hydrochloric Acid → (4-Phenylbutyl)phosphonic acid

HRID 651942

Reaction equation

HRID 651942 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P:11]([OH:13])[OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[Mn]([O-])(=O)(=O)=[O:17].[K+].Cl.S(=O)(O)[O-].[Na+]>CC(C)=O.O.C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P:11](=[O:17])([OH:13])[OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 132746654-Phenylbutylphosphonous acidHCID 23665763Sodium Bisulfite

Product 1

HCID 13687984(4-Phenylbutyl)phosphonic acid

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

4-Phenylbutylphosphonous acid (47.19 gm, 0.238 mole) was dissolved in acetone (250 ml) and diluted with water (50 ml). Sodium hydroxide solution (9.5 gm, 0.238 mole) in water (50 ml) was added to it to get pH=7.0. The reaction mixture was cooled to 20° C. and potassium permanganate solution (22.5 gm, 0.142 mole) in water (250 ml) was added to it with stirring and maintaining the temperature around 20°-2 ° C. After the addition (15 minutes), the reaction mixture was stirred for 15 minutes at room temperature, acidified to pH 0 using concentrated HCl acid and saturated sodium bisulphite solution was added to it to get a white cloudy precipitate. Standard extractive workup using ethyl acetate followed by crystallization from ethyl acetate/hexane produced the title compound in 87% (44.16 gm) yield, m.p. 93° C.

Workup

  1. customto get pH=7.0
  2. temperaturemaintaining the temperature around 20°-2 ° C
  3. additionAfter the addition (15 minutes)
  4. stirringthe reaction mixture was stirred for 15 minutes at room temperature
  5. additionwas added to it
  6. customto get a white cloudy precipitate
  7. customfollowed by crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8bff35037c9c42e6be58d76192f8db73
Source dataset
uspto-grants-1987_06
Patent number
US04670193

Linked notes

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