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

HRID 64848

Reaction equation

HRID 64848 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].C(Cl)(=O)C([Cl:19])=O>C(Cl)Cl>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([Cl:19])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 3672Ibuprofen, (+-)-HCID 65578Oxalyl chloride2×

Product 1

HCID 595157alpha-Methyl-4-(2-methylpropyl)benzeneacetyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well-stirred solution consisting of 3.1 g. (0.015 mole) of α-(4-isobutylphenyl)propionic acid (ibuprofen) dissolved in 200 ml. of methylene chloride, there were added 3.8 g. (0.030 mole) of oxalyl chloride. The resulting reaction mixture was refluxed for a period of two hours and then cooled to room temperature. The clear colorless solution so obtained was thereafter concentrated in vacuo to dryness to yield a residue that was substantially free of solvent and excess oxalyl chloride. In this way, there was readily obtained substantially pure α-(4-isobutylphenyl)-propionyl chloride in the form of a clear colorless oil. The latter product was used as such in the next reaction step without any purification being necessary. The yield of product was assumed to be quantitative.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for a period of two hours
  3. customThe clear colorless solution so obtained
  4. concentrationwas thereafter concentrated in vacuo to dryness
  5. customto yield a residue that

Sources & evidence

ORD record
ord-2ce7a49af1ff4c299ebec8617be78216
Source dataset
uspto-grants-1986_09
Patent number
US04610982

Linked notes

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