2-Tert-Butylphenol → HCID 61343954, compound

HRID 1913305Notes

Reaction equation

HRID 1913305 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.O>[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

6

Reactant 3

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

Product 1

HCID 61343954HCID 61343954, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(tert-butyl)phenol (21.0 g, 140 mmol) and propargyl bromide (18.8 mL, 168 mmol) in acetonitrile (250 mL) was added potassium carbonate (23.3 g, 168 mmol). The reaction was stirred at ambient temperature for two days. The reaction mixture was diluted with water (50 mL) and extracted diethyl ether (2×150 mL). The combined organic extracts were concentrated to provide 23.7 g (90%) of the title compound which was used without further purification. 1H NMR (300 MHz, DMSO-d6) δ 7.26-7.14 (m, 2H), 7.02 (d, J=8.0 Hz, 1H), 6.94-6.86 (m, 1H), 4.83 (d, J=2.4 Hz, 2H), 3.55 (t, J=2.4 Hz, 1H), 1.34 (s, 9H).

Workup

  1. extractionextracted diethyl ether (2×150 mL)
  2. concentrationThe combined organic extracts were concentrated

Sources & evidence

ORD record
ord-942df14f3c2a4c868d05fb1f7bdec8a8
Source dataset
uspto-grants-2013_12
Patent number
US08609692B2

Reaction notes

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