2-Tert-Butylphenol → HCID 61343954, compound

HRID 1517644Notes

Reaction equation

HRID 1517644 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, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Tert-butylphenol (15.02 g, 15.4 ml, 100 mmol), propargyl bromide (14.3 ml of 80% in toluene, 128 mmol), and potassium carbonate (17.66 g, 128 mmol) were stirred together in 200 ml of acetonitrile at ambient temperature for 5 days. 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, and filtered. The solvent was evaporated under reduced pressure to give 18.86 g of the title compound which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 7.30 (dd, J=7.80, 1.70 Hz, 1 H), 7.15-7.22 (m, 1 H), 6.90-6.98 (m, 2 H), 4.73 (d, J=2.37 Hz, 2 H), 2.48 (t, J=2.37 Hz, 1 H), 1.39 (s, 9 H). MS (DCI) m/e 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 was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e4175a384c324610aa5287028ee0c3c9
Source dataset
uspto-grants-2012_07
Patent number
US08232309B2

Reaction notes

Loading…