Triphenyl phosphite → 3-(1,1-Dimethylethyl)benzenepropanal

HRID 2369774Notes

Reaction equation

HRID 2369774 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[CH2:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:13]1([O:19]P(OC2C=CC=CC=2)OC2C=CC=CC=2)C=CC=CC=1.[H][H].[C]=O>C1(C)C=CC=CC=1.C/C(/O)=C/C(C)=O.[C-]#[O+].[C-]#[O+].[Rh]>[C:1]([C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][CH:13]=[O:19])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 7540Triphenyl phosphiteHCID 21930490HCID 21930490, compoundHCID 178418361HCID 178418361, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 574294073-(1,1-Dimethylethyl)benzenepropanalYield 13,005.7%

Reagents, catalysts & solvents 2

HCID 5377512Rhodium, dicarbonyl(2,4-pentanedionato)-CatalystHCID 1140TolueneSolvent

Procedure

Acetylacetonatodicarbonylrhodium (I) (41 mg, 0.1 mol %) of 1-tert-butyl-3-vinylbenzene (29 g, 0.16 mol) and a solution of triphenylphosphite (261 mg, 0.99 mmol) in 88 g of toluene were added to a 250 mL autoclave vessel. The vigorously stirred reaction mixture heated for 6 h under a pressure of syn gas (mixture of hydrogen and carbon monoxide in a ratio 1:1-1 Bar), at 80° C. The crude reaction mixture was concentrated in vacuo and chromatographed on a silica gel column with 3% MTBE in hexane as elution agent to give 3-(3-tert-butylphenyl)propanal (24.5 g, gc purity>82%; yield=63%).

Workup

  1. customThe vigorously stirred reaction mixture
  2. temperatureheated for 6 h under a pressure of syn gas (
  3. customThe crude reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customchromatographed on a silica gel column with 3% MTBE in hexane as elution agent

Sources & evidence

ORD record
ord-eb24ee1bcb9c4a4a960c344a33ded1e1
Source dataset
uspto-grants-2014_04
Patent number
US08709994B2

Reaction notes

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