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4-tert-Butylphenol → 4-(4-tert-Butylphenoxy)benzaldehyde

HRID 1586093
Notes
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Reaction equation

HRID 1586093 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([O:20][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:18][CH:19]=1)([CH3:13])([CH3:11])[CH3:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 108248404-(4-tert-Butylphenoxy)benzaldehydeYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-fluorobenzaldehyde (2.0 g, 0.0161 mol), 4-tert-butylphenol (2.42 g, 0.161 mol), and K2CO3 (9.0 g, 0.065 mol) in DMF (50 mL) was heated at 80° C. After 6 h, the reaction mixture was filtered into ice/water and the product was extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO4), concentrated and chromatographed with 1:1 hexane/ethyl acetate to give 3.9 g (95%) of 4-(4-tert-butylphenoxy)benzaldehyde.

Workup

  1. filtrationthe reaction mixture was filtered into ice/water
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customchromatographed with 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-c3b441a713bf4699b13d7e77dd392feb
Source dataset
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05942532

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes