4-Hydroxybenzaldehyde → 4-Isopropoxybenzaldehyde

HRID 1731582Notes

Reaction equation

HRID 1731582 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].I[CH:19]([CH3:21])[CH3:20]>CC(=O)CC>[CH:19]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 6362Isopropyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 2500774-Isopropoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-hydroxybenzaldehyde (20 g), anhydrous potassium carbonate (25 g), potassium iodide (0.5 g) and 2-iodopropane (27 g) in 2-butanone (300 ml) was heated overnight, under reflux, with stirring, cooled, filtered and evaporated to dryness. The residue was dissolved in diethyl ether, washed with aqueous sodium hydroxide and brine, dried (magnesium sulphate), filtered and evaporated to dryness. Distillation of the residue gave the title compound, bp 108°-112°/3 mm as an oil.

Workup

  1. temperaturewas heated overnight
  2. temperatureunder reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in diethyl ether
  7. washwashed with aqueous sodium hydroxide and brine
  8. dry with materialdried (magnesium sulphate)
  9. filtrationfiltered
  10. customevaporated to dryness
  11. distillationDistillation of the residue

Sources & evidence

ORD record
ord-9cb9c55ae67d4cbaa696f5a9c8cfa4d3
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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