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

HRID 1091828Notes

Reaction equation

HRID 1091828 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 3-4 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-e83c421a84af4a9e9d1aadea8419f304
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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