p-Toluenesulfonic acid monohydrate → 4-(3,3-Dimethyl-butyryl)-benzaldehyde

HRID 911702Notes

Reaction equation

HRID 911702 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:17])[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][CH:6]=1)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([C:8]1[CH:7]=[CH:6][C:5]([CH:4]=[O:3])=[CH:10][CH:9]=1)=[O:17]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 576563621-[4-(Diethoxymethyl)-phenyl]-3,3-dimethylbutan-1-one

Product 1

HCID 576561564-(3,3-Dimethyl-butyryl)-benzaldehydeYield 65.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 1-[4-(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-4020fa0628e84750b7d91e2e967badb4
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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