3,3-Dimethylbutanal → 4-(3,3-Dimethyl-butyryl)-benzaldehyde

HRID 2041564Notes

Reaction equation

HRID 2041564 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=[O:5].[OH2:8].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12](S(O)(=O)=O)=[CH:11][CH:10]=1>CC(C)=O>[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][C:4]([C:12]1[CH:13]=[CH:14][C:9]([CH:19]=[O:8])=[CH:10][CH:11]=1)=[O:5]

Participants

4

Reactant 2

HCID 763353,3-DimethylbutanalHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 576561564-(3,3-Dimethyl-butyryl)-benzaldehydeYield 650.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 144-(diethoxymethyl)-phenyl]-3,3-dimethylbutan-1-one (3.49 g, 12.55 mmol) in acetone (50 mL) Add p-toluenesulfonic acid monohydrate (238 mg, 1.256 mmol). Heat the mixture under reflux for 3 h. Concentrate in vacuo and partition the residue between water and EtOAc. Extract the aqueous phase three times with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (9:1) to give the desired intermediate as a colorless oil (1.67 g, 65%).

Workup

  1. temperatureHeat the mixture
  2. temperatureunder reflux for 3 h
  3. concentrationConcentrate in vacuo
  4. custompartition the residue between water and EtOAc
  5. extractionExtract the aqueous phase three times with EtOAc
  6. dry with materialDry the combined organic extracts over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-d5618db1376e401093c1d4776c92bc61
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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