Butyl iodide → 4-Butoxy-2,6-dimethylbenzaldehyde

HRID 1382164Notes

Reaction equation

HRID 1382164 reaction equation
I[CH2:2][CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].[CH3:12][C:13]1[CH:20]=[C:19]([OH:21])[CH:18]=[C:17]([CH3:22])[C:14]=1[CH:15]=[O:16]>C(C(C)=O)C>[CH2:2]([O:21][C:19]1[CH:18]=[C:17]([CH3:22])[C:14]([CH:15]=[O:16])=[C:13]([CH3:12])[CH:20]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 5910722,6-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 212741904-Butoxy-2,6-dimethylbenzaldehydeYield 92%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1-Iodobutane (9.2 g; 50 mmole) and potassium carbonate (6.9 g; 50 mmole) were added to a solution of 2,6-dimethyl-4-hydroxybenzaldehyde (7.5 g; 50 mmole) in methyl ethyl ketone (150 ml). The mixture was heated under reflux with stirring for 20 hours and then evaporated to dryness. The residue was dissolved in dichloromethane and washed with water, then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give 4-butoxy-2,6-dimethylbenzaldehyde (9.4 g; 92.0%). The product was obtained as a yellow oil and was characterized by its proton magnetic resonance spectrum, the details of which are recorded in Table 2 below.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-179b738ace5042689b38d52d16fd7515
Source dataset
uspto-grants-1989_02
Patent number
US04806141

Reaction notes

Loading…