Phenol → [(3-Methylbut-3-en-1-yl)oxy]benzene

HRID 1382912Notes

Reaction equation

HRID 1382912 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]([CH2:11][CH2:12]OS(C)(=O)=O)=[CH2:10].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:10][C:9]([CH2:11][CH2:12][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH2:8]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 12744890HCID 12744890, compound

Product 1

HCID 12441681[(3-Methylbut-3-en-1-yl)oxy]benzeneYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 24.4 g (260 mmol) of phenol, 47.0 g (286 mmol) of 2-methyl-4-methylsulfonyloxy-1-butene, 107 g (780 mmol) of potassium carbonate and 300 ml of N,N-dimethylformamide was stirred and heated at 80° C. for 6 hours, and then it was poured onto 500 ml of ice-water. The resulting mixture was extracted with hexane and the combined extracts were dried (MgSO4) and evaporated in vacuo to give the title compound as an oil (28.0 g, 66% yield).

Workup

  1. extractionThe resulting mixture was extracted with hexane
  2. dry with materialthe combined extracts were dried (MgSO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-172f4c3a4ef745be87ed9927b2e89c5c
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

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