Ibuprofen, (+-)- → β-Methyl-4-(2-methylpropyl)benzeneethanol

HRID 1031402Notes

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(C1C=CC=CC=1)C(C)C.C1OC1C>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:15])[CH2:12][OH:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

Reactant 3

HCID 3672Ibuprofen, (+-)-2×

HCID 6378Propylene Oxide

HCID 10870Isobutylbenzene

Product 1

HCID 595160β-Methyl-4-(2-methylpropyl)benzeneethanol

Procedure

preparation of the pharmaceutically-active compound 2-(4-isobutylphenyl) propionic acid, i.e. ibuprofen, by reacting isobutylbenzene with propylene oxide to provide the intermediate 2-(4-isobutylphenyl) propanol followed by oxidation of the alcohol to the corresponding carboxylic acid;

Sources & evidence

ORD record: ord-6a090495c3964c09ab29171170ba379f
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04954325

Reaction notes

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