M-Cresol → 1-Methyl-3-[(prop-2-yn-1-yl)oxy]benzene

HRID 2377272Notes

Reaction equation

HRID 2377272 reaction equation
[C:1]1(S(OCC#C)(=O)=O)[CH:6]=CC=C[CH:2]=1.[CH:14]1[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([O:20][CH2:6][C:1]#[CH:2])[CH:14]=1

Participants

5

Reactant 3

HCID 342M-CresolHCID 11430Potassium CarbonateHCID 802732-Propyn-1-ol, 1-benzenesulfonate

Product 1

HCID 123605181-Methyl-3-[(prop-2-yn-1-yl)oxy]benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of propargyl benzenesulfonate (1.0 g, 5.1 mmol), m-cresol (0.55 mL, 5.1 mmol) and potassium carbonate (1.1 g, 7.65 mmol) in acetone (40 mL) was stirred at about 56 C for about 2 days. The mixture was cooled, filtered and the solvent was carefully distilled off at atmospheric pressure. The residue was purified by flash chromatography on silica gel using diethyl ether/n-pentane (1:9) as eluent to provide Example 614. 1H NMR (500 MHz, CDCl3): □ 2.33 (s, 3H), 2.50 (t, J=3.0 Hz, 1H), 4.66 (d, J=3.0 Hz, 2H), 6.77-6.82 (m, 3H), 7.15-7.21 (m, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. distillationthe solvent was carefully distilled off at atmospheric pressure
  4. customThe residue was purified by flash chromatography on silica gel
  5. customto provide Example 614

Sources & evidence

ORD record
ord-677dbeda96bb41128090b3063ecc1811
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

Loading…