Potassium Iodide → 4-Benzyloxy-3-propoxybenzaldehyde

HRID 987867Notes

Reaction equation

HRID 987867 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:9][CH2:10][CH2:11]Br.[CH2:13]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][C:22]=1[OH:29])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CS(C)=O>[CH2:13]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][C:22]=1[O:29][CH2:9][CH2:10][CH3:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

Product 1

HCID 229870904-Benzyloxy-3-propoxybenzaldehydeYield 89.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.15 g (15.6 mmol) of potassium carbonate, 0.20 g (1.22 mmol) of potassium iodide and 1.20 ml (13.2 mmol) of n-propyl bromide were added to a solution of 2.73 g (12.0 mmol) of 4-benzyloxy-3-hydroxybenzaldehyde in 18 ml of dimethyl sulfoxide (DMSO) and were allowed to react for 24 hours at 60° C. Thereafter, the reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water and the organic phase was washed several times with saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated down. Chromatography of the residue over 50 g of silica gel using toluene gave 2.90 g of 4-benzyloxy-3-propoxybenzaldehyde.

Workup

  1. customto react for 24 hours at 60° C
  2. custompartitioned between ethyl acetate and water
  3. washthe organic phase was washed several times with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated down

Sources & evidence

ORD record
ord-65ecc0aa62774f3baa22028809276092
Source dataset
uspto-grants-2003_10
Patent number
US06632909B2

Reaction notes

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