Acetonitrile → HCID 101961358, compound

HRID 63623

Reaction equation

HRID 63623 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](#[N:17])[CH3:16].[C:18](O)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>>[O:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][CH2:18][CH2:16][C:15]#[N:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6386tert-ButanolHCID 11430Potassium CarbonateHCID 128423-Phenoxyphenol

Product 1

HCID 101961358HCID 101961358, compoundYield 726.2%

Procedure

To a solution of 3-phenoxyphenol (3.0 g, 16.1 mmol) in acetonitrile (10.6 mL, 161 mmol) was added tert-BuOH (120 mg, 1.6 mmol) and K2CO3 (225 mg, 1.6 mmol). The mixture was refluxed for 2 days. The reaction was filtered and concentrated, and the residue was purified by HPLC to get give 2.78 g (72%) of the title compound as a colorless gum. 1H NMR (400 MHz, CDCl3): δ 2.80 (2H, t, J=6.0 Hz), 4.15 (2H, t, J=6.0 Hz), 6.55 (1H, s), 6.64 (2H, d, J=8.0 Hz), 7.02 (2H, d, J=7.6 Hz), 7.12 (1H, t, J=7.2 Hz), 7.23 (1H, t, J=8.0 Hz) 7.35 (2H, t, J=8.0 Hz).

Workup

  1. temperatureThe mixture was refluxed for 2 days
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customthe residue was purified by HPLC
  5. customto get

Sources & evidence

ORD record
ord-619d6cbd296c490ba32d2b4dbc72ab6e
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Linked notes

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