Triphenylphosphine → 3-(p-Methylphenyl)propanal

HRID 1952958Notes

Reaction equation

HRID 1952958 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29](Cl)=[O:30])=[CH:23][CH:22]=1>CC(C)=O>[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH:29]=[O:30])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 130292003-(4-Methylphenyl)propanoyl chloride

Product 1

HCID 648123-(p-Methylphenyl)propanal

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of triphenylphosphine (0.117 moles, 30.8 g) in acetone (200 ml) is added under a nitrogen stream at r.t. with Cu (I) bis-(triphenyl-phosphine)-tetrahydroborate (0.067 moles, 40.69 g), then 3-(4-methylphenyl)propanoyl chloride (0.055 moles, 10 g) dissolved in acetone (85 ml) is dropped in 45'. The mixture is stirred at r.t. under nitrogen for 1 h. The precipitated solid is filtered, washing with acetone and the filtrate is evaporated under vacuum. The residue is dissolved in chloroform (340 ml), added with cuprous chloride (0.135 moles, 13.38 g) and stirred under nitrogen stream for 1 h at r.t. The mixture is filtered through celite, the filtrate is evaporated to dryness and the resulting residue is taken up into ethyl ether and petroleum ether, filtered and evaporated under vacuum to obtain an oil. Yield: 6.7 g (83%)

Workup

  1. additionis dropped in 45'
  2. filtrationThe precipitated solid is filtered
  3. washwashing with acetone
  4. customthe filtrate is evaporated under vacuum
  5. dissolutionThe residue is dissolved in chloroform (340 ml)
  6. stirringstirred under nitrogen stream for 1 h at r.t
  7. filtrationThe mixture is filtered through celite
  8. customthe filtrate is evaporated to dryness
  9. filtrationfiltered
  10. customevaporated under vacuum
  11. customto obtain an oil

Sources & evidence

ORD record
ord-6809b637859049dc9b3ad624c7f55e31
Source dataset
uspto-grants-2000_09
Patent number
US06114391

Reaction notes

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