2-Tert-Butylphenol → HCID 61343954, compound

HRID 1662136Notes

Reaction equation

HRID 1662136 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH2:12](Br)[C:13]#[CH:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:14][C:13]#[CH:12])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 69232-Tert-ButylphenolHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 61343954HCID 61343954, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-tert-butylphenol (Aldrich, 15.02 g, 15.4 ml, 100 mmol), propargyl bromide (80% in toluene, 14.3 ml, 128 mmol) and potassium carbonate (17.66 g, 128 mmol) were stirred together in acetonitrile (200 mL) for 5 days at ambient temperature. The solvent was removed under reduced pressure, and the residue taken into water and extracted with diethyl ether. The organic layers were combined, dried with magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.39 (s, 9H), 2.48 (t, J=2.37 Hz, 1H), 4.73 (d, J=2.37 Hz, 2H), 6.90-6.98 (m, 2H), 7.15-7.22 (m, 1H), 7.30 (dd, J=7.80, 1.70 Hz, 1H). MS (DCI) m/z 206 (M+NH4)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with diethyl ether
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-b302f25c5fc14982beed8f54a8c62a9e
Source dataset
uspto-grants-2011_10
Patent number
US08030504B2

Reaction notes

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