Guaiacol → 4-(4'-Methylphenoxy)hexyl bromide

HRID 327276Notes

Reaction equation

HRID 327276 reaction equation
CO[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[OH-].[K+].Br[CH:13]([Br:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:20]O>CC(C)=O>[CH3:20][C:7]1[CH:6]=[CH:5][C:4]([O:9][CH:16]([CH2:17][CH3:18])[CH2:15][CH2:14][CH2:13][Br:19])=[CH:3][CH:8]=1

Participants

6

Reactant 4

HCID 460GuaiacolHCID 887Methanol2×HCID 14797Potassium HydroxideHCID 118068541,1-Dibromohexane

Product 1

HCID 190238784-(4'-Methylphenoxy)hexyl bromideYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 62 g of methoxy phenol in 50 ml of methanol was added into a solution of 33.75g of potassium hydroxide in 100 ml of methanol. The resulting solution was added dropwisely and slowly into 1 mole of α, -dibromohexane in 200 ml of acetone within 1 hour. After a reflux of the mixture for 1 hour, the mixture was concentrated and then diluted with water. The oil layer of the mixture was extracted with ethyl ether. Then, the ethyl ether layer was filtered and the filtrate was extracted with water. The solution was dried by calcium chloride, and 4-(4'-methoxyphenoxy) hexylbromide (compound 1, with a yield of 62% was obtained by distillation under reduced pressure.

Workup

  1. temperatureAfter a reflux of the mixture for 1 hour
  2. concentrationthe mixture was concentrated
  3. additiondiluted with water
  4. extractionThe oil layer of the mixture was extracted with ethyl ether
  5. filtrationThen, the ethyl ether layer was filtered
  6. extractionthe filtrate was extracted with water
  7. dry with materialThe solution was dried by calcium chloride, and 4-(4'-methoxyphenoxy) hexylbromide (compound 1
  8. customwith a yield of 62% was obtained by distillation under reduced pressure

Sources & evidence

ORD record
ord-346bdecd9f494570a910441b621dfdb1
Source dataset
uspto-grants-1993_12
Patent number
US05272234

Reaction notes

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