(4-Ethynylphenyl)(4-fluorophenyl)methanol → (4-Ethynylphenyl)(4-fluorophenyl)methanone

HRID 710320Notes

Reaction equation

HRID 710320 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[OH:10])=[CH:5][CH:4]=1)#[CH:2]>O1CCOCC1.O=[Mn]=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[O:10])=[CH:7][CH:8]=1)#[CH:2]

Participants

4

Reactant 1

HCID 86661773(4-Ethynylphenyl)(4-fluorophenyl)methanol

Product 1

HCID 23352815(4-Ethynylphenyl)(4-fluorophenyl)methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

The product of Step C was dissolved in anhydrous dioxane (20 ml) and to it MnO2 (0.5 g) was added. The suspension was stirred at reflux for 6 h and then filtered through Celite. The filtrate was distilled off and the residue was purified by FCC (SiO2) to give the product (0.18 g; 89%), as creamy paste. 1H-NMR (CDCl3) 3.24 (s, 1H); 7.15 (tr, 2H, J=8.73 Hz); 7.60 (d, 2H, J=6.69 Hz); 7.71 (d, 2H, J=6.58 Hz); 7.78-7.84 (m, 2H).

Workup

  1. additionwas added
  2. temperatureat reflux for 6 h
  3. filtrationfiltered through Celite
  4. distillationThe filtrate was distilled off
  5. customthe residue was purified by FCC (SiO2)
  6. customto give the product (0.18 g; 89%)

Sources & evidence

ORD record
ord-a3f58eee58ab42aaa2844e2f227e4cea
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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