3-Hydroxybenzaldehyde → 3-Isopropoxybenzaldehyde

HRID 1510150Notes

Reaction equation

HRID 1510150 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].I[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].O>C(O)(C)C>[CH:11]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 7129143-Isopropoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a 1 molar solution of 3-hydroxybenzaldehyde (10 g, 0.819 moles) in isopropyl alcohol (820 mL) was added 2-iodopropane (146.2 g, 0.860 moles) followed by powdered potassium carbonate (339.5 g, 0.457 moles) and the mixture was heated to reflux under nitrogen for a minimum of 8 hrs. The reaction was complete by TLC. Water was added to the cooled reaction until all salts were dissolved. The mixture was extracted with ether three times. The combined ether extracts were washed with water, 2 M NaOH and again with water until clear (three times) then brine. The organic layer was dried over magnesium sulfate and filtered and evaporated to give the desired product as a pale oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under nitrogen for a minimum of 8 hrs
  3. dissolutionwere dissolved
  4. extractionThe mixture was extracted with ether three times
  5. washThe combined ether extracts were washed with water, 2 M NaOH and again with water until clear (three times)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-426c0bfec0ed48ae87e5a05159984306
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

Loading…