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

HRID 548965Notes

Reaction equation

HRID 548965 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 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a well stirred solution of guaiacol (10.0 g, 80.55 mmol) and propargyl bromide (11.5 g, 96.66 mmol) in DMF (100 mL) was added anhydrous K2CO3 (22.0 g, 161.2 mmol) and the mixture was stirred at room temperature for 34 hours. The mixture was then filtered to remove inorganic material. Filtrate was concentrated under vacuo and diluted with water (250 mL). It was then extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with water (2×100 mL) and dried over anhydrous sodium sulfate. Removal of solvent under vacuo gave the product (13.0 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 (250 mL)
  5. extractionIt was then extracted with ethyl acetate (3×100 mL)
  6. washThe combined organic layers were washed with water (2×100 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customRemoval of solvent under vacuo

Sources & evidence

ORD record
ord-54e2de8e86ec41e4a7b47add961a74f2
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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