Triphenylphosphine → Ibuprofenal

HRID 1904900Notes

Reaction equation

HRID 1904900 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12](Cl)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(C)=O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:15])[CH:12]=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 595157alpha-Methyl-4-(2-methylpropyl)benzeneacetyl chloride

Product 1

HCID 595156Ibuprofenal

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
20 °C

Procedure

An aliquot of the so obtained (2RS)-2-(4-isobutylphenyl)-propanoyl chloride (44.8 g; 0.199 moles) is dissolved in acetone (200 ml); this solution is added dropwise to a suspension of triphenyl phosphine (112 g; 0.427 moles) and bistriphenyl phosphine cupper boron hydride (128 g; 0.212 moles) in acetone (600 ml) kept under stirring at 20° C.

Sources & evidence

ORD record
ord-c8961b7cc9444f9cbfe877e15011c9ed
Source dataset
uspto-grants-1989_06
Patent number
US04840936

Reaction notes

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