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

HRID 1807911Notes

Reaction equation

HRID 1807911 reaction equation
[CH3:1][C:2](=[CH2:6])[CH2:3][CH2:4][OH:5].[C:7]1(O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[CH3:6][C:2](=[CH2:1])[CH2:3][CH2:4][O:5][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 129883-Methyl-3-buten-1-olHCID 97268Di-tert-butyl azodicarboxylate

Product 1

HCID 12441681[(3-Methylbut-3-en-1-yl)oxy]benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 3-methyl-3-buten-1-ol (1.17 ml) in tetrahydrofuran (30 ml) were added sequentially phenol (1.32 g), triphenylphosphine (3.85 g) and di-tert-butyl azodicarboxylate (3.27 g). The mixture was heated at 70° C. overnight and then was concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0->70:30) to give (3-methyl-but-3-enyloxy)-benzene (2.06 g, quant.) as a colourless semi-solid which crystallized on standing.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0->70:30)

Sources & evidence

ORD record
ord-7eb7d1f5a1844968a4cea0a3d0bc0072
Source dataset
uspto-grants-2013_01
Patent number
US08357712B2

Reaction notes

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