2-Tert-Butylphenol → HCID 61343954, compound

HRID 1844682Notes

Reaction equation

HRID 1844682 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].[CH:12]#[C:13][CH2:14]Br.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

To a stirred solution of 2-(tert-butyl)phenol (5.0 g, 34 mmol) and progargyl bromide (4.8 g, 40 mmol) in dry ACN (50 mL) was added K2CO3 (5.5 g, 40 mmol) and the solution was stirred for 2 d at rt, concentrated, redissolved in water and extracted with Et2O. The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by CC (PE) to give compound P4a (4.5 g, 72%) as an oil.

Workup

  1. concentrationconcentrated
  2. dissolutionredissolved in water
  3. extractionextracted with Et2O
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by CC (PE)
  8. customto give compound P4a (4.5 g, 72%) as an oil

Sources & evidence

ORD record
ord-5bbd272de6fe4200a3ade9fd4394541e
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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