4-Hydroxybenzaldehyde → 4-[5-(3-Methyl-5-isoxazolyl)pentyloxy]benzaldehyde

HRID 1905522Notes

Reaction equation

HRID 1905522 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[O:20][N:19]=[C:18]([CH3:21])[CH:17]=1.[OH-].[K+]>C(#N)C>[CH3:21][C:18]1[CH:17]=[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[O:20][N:19]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 14797Potassium HydroxideHCID 135440465-(5-Bromopentyl)-3-methylisoxazole

Product 1

HCID 64834254-[5-(3-Methyl-5-isoxazolyl)pentyloxy]benzaldehydeYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 7.2 g of 4-hydroxybenzaldehyde, 14.6 g of 5-(5-bromopentyl)-3-methylisoxazole, 4 g of potassium hydroxide in 100 ml of acetonitrile was heated at reflux for 1.5 hours. The reaction mixture was cooled and filtered, the solvent removed, and the residue recrystallized from isopropyl acetate-hexane to give 10.8 g of 4-[5-(3-methyl-5-isoxazolyl)pentyloxy]benzaldehyde as a pale yellow powder.

Workup

  1. temperatureat reflux for 1.5 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customthe solvent removed
  5. customthe residue recrystallized from isopropyl acetate-hexane

Sources & evidence

ORD record
ord-8b10ff1da1104a44b9eaf87787e80a76
Source dataset
uspto-grants-1989_06
Patent number
US04843087

Reaction notes

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