Salicylaldehyde → 2-(5-Chloropentyloxy)benzaldehyde

HRID 1034169Notes

Reaction equation

HRID 1034169 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>CC(O)C>[Cl:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 960701-Bromo-5-chloropentane

Product 1

HCID 190236192-(5-Chloropentyloxy)benzaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 100 g (0.82 mol) of salicylaldehyde in 2000 ml of iPrOH was added 228 g (1.23 mol) of 1-bromo-5-chloro-pentane, followed by 113 g (0.82 mol) of potassium carbonate. The reaction was refluxed under nitrogen and followed by TLC. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure to remove all solvent. The liquid residue was purified by fractional distillation under reduced pressure: 1st fraction: 45°-50° C., 0.4 mm Hg [Br(CH2)5Cl] 2nd fraction: 159.8 g (86% yield), 145°-150° C., 0.3 mm Hg colorless liquid product. The remaining residue proved to a dialdehyde by-product. TLC: Starting aldehyde Rf=0.46 (30% ether/pet. ether). Desired aldehyde: Rf=0.35. By-product: Rf=0.15.

Workup

  1. temperatureThe reaction was refluxed under nitrogen
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto remove all solvent
  5. distillationThe liquid residue was purified by fractional distillation under reduced pressure
  6. custom45°-50° C., 0.4 mm Hg [Br(CH2)5Cl] 2nd fraction
  7. custom159.8 g (86% yield), 145°-150° C., 0.3 mm Hg colorless liquid product

Sources & evidence

ORD record
ord-3747b3fef54f4a5e92bdc4bd4812bd6d
Source dataset
uspto-grants-1994_05
Patent number
US05314887

Reaction notes

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