Ibuprofen, (+-)- → alpha-Methyl-4-(2-methylpropyl)benzeneacetyl chloride

HRID 2164233Notes

Reaction equation

HRID 2164233 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12](O)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].P(Cl)(Cl)(Cl)(Cl)[Cl:17]>C(OCC)C>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([Cl:17])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 3672Ibuprofen, (+-)-HCID 24819Phosphorus pentachloride

Product 1

HCID 595157alpha-Methyl-4-(2-methylpropyl)benzeneacetyl chlorideYield 98.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.66 g of 2-(4-isobutylphenyl)propionic acid is agitated in 150 ml of diethyl ether with 5.04 g of phosphorus pentachloride for one hour at 20° C. The mixture is then concentrated under vacuum, thus obtaining 5.02 g of 2-(4-isobutylphenyl)propionyl chloride. This compound is reacted with trimethyl phosphite as described in Example 2, thus producing the dimethyl ester of 2-(4-isobutylphenyl)propionylphosphonic acid. The dimethyl ester is reacted with dimethyl phosphite under the conditions described in Example 2, thus obtaining the 2-(4-isobutylphenyl)-1-hydroxypropane-1,1-bis(phosphonic acid dimethyl ester).

Workup

  1. concentrationThe mixture is then concentrated under vacuum

Sources & evidence

ORD record
ord-ff185a0fe2094cfba28b47b08c165ad3
Source dataset
uspto-grants-1985_03
Patent number
US04503049

Reaction notes

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