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

HRID 728998Notes

Reaction equation

HRID 728998 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 4-hydroxybenzaldehyde, 14.6 g 5-(5-bromopentyl)-3-methylisoxazole, 4 g potassium hydroxide in 100 ml 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 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-bd6c43383674461888d7a152f67c64df
Source dataset
uspto-grants-1991_09
Patent number
US05051437

Reaction notes

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