4-Hydroxybenzaldehyde → 4-[(Undec-10-en-1-yl)oxy]benzaldehyde

HRID 987344Notes

Reaction equation

HRID 987344 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12].[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[I-]>C(C(C)=O)C>[CH2:2]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12]

Participants

7

Reactant 5

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 28414811-Bromo-1-undecene

Product 1

HCID 186710574-[(Undec-10-en-1-yl)oxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 11-bromoundec-1-ene (2.02 g), 4-hydroxy-benzaldehyde (1.06 g, 8.6 mmol), potassium carbonate, potassium iodide and tetra-n-butylamomnium iodide was heated at reflux in methyl ethyl ketone (10 ml) for 16 hours. After cooling, the solids were filtered off and washed with acetone. The combined organic fractions were evaporated to dryness. The crude product obtained was filtered through a pad of silica gel which was eluted with petroleum ether (b.p. 40-60° C.) to remove the excess of bromoundecene. The silica gel was then eluted with acetone and the acetone fractions evaporated under reduced pressure to yield the title compound.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. filtrationthe solids were filtered off
  4. washwashed with acetone
  5. customThe combined organic fractions were evaporated to dryness
  6. customThe crude product obtained
  7. filtrationwas filtered through a pad of silica gel which
  8. washwas eluted with petroleum ether (b.p. 40-60° C.)
  9. customto remove the excess of bromoundecene
  10. washThe silica gel was then eluted with acetone
  11. customthe acetone fractions evaporated under reduced pressure

Sources & evidence

ORD record
ord-95d37ed23318491194e3f5140aeec88c
Source dataset
uspto-grants-2003_10
Patent number
US06630128B1

Reaction notes

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