Guaiacol → Benzene, 1-methoxy-2-(2-propen-1-yloxy)-

HRID 1091856Notes

Reaction equation

HRID 1091856 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].[CH2:10](Br)[C:11]#[CH:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:9][O:8][C:1]1[CH:7]=[CH:6][CH:5]=[CH:4][C:2]=1[O:3][CH2:12][CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 77777Benzene, 1-methoxy-2-(2-propen-1-yloxy)-Yield 74,392.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a well stirred solution of guaiacol (100.0 g, 0.805 moles) and propargyl bromide (135 g, 0.966 mmoles) in DMF (600 mL) was added anhydrous K2CO3 (222.0 g, 1.61 moles) and the mixture was stirred at room temperature for 3-4 hours. The mixture was then filtered to remove inorganic material. Filtrate was concentrated under vacuo and diluted with water (2.5 L). It was then extracted with ethyl acetate (3×1.0 L). The combined organic layers were washed with water (2×1.0 L) and dried over anhydrous sodium sulfate. Removal of solvent under vacuo gave the product (118.0 g) as brown oil.

Workup

  1. filtrationThe mixture was then filtered
  2. customto remove inorganic material
  3. concentrationFiltrate was concentrated under vacuo
  4. additiondiluted with water (2.5 L)
  5. extractionIt was then extracted with ethyl acetate (3×1.0 L)
  6. washThe combined organic layers were washed with water (2×1.0 L)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customRemoval of solvent under vacuo

Sources & evidence

ORD record
ord-36e176b9052b476aa90521cf982c9af7
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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