Monobenzone → 4-(4-Benzyloxy-phenoxy)-phthalonitrile

HRID 409269Notes

Reaction equation

HRID 409269 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([C:19]1[CH:20]=[C:21]([C:27]#[N:28])[C:22](=[CH:25][CH:26]=1)[C:23]#[N:24])([O-])=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:19]2[CH:20]=[C:21]([C:27]#[N:28])[C:22](=[CH:25][CH:26]=2)[C:23]#[N:24])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 7466114-(4-Benzyloxy-phenoxy)-phthalonitrileYield 111.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-benzyloxyphenol (14.53 g, 72.6 mmol), 4-nitrophthalonitrile (10.47 g, 60.5 mmol), potassium carbonate (16.69 g, 120.9 mmol), and acetone (170 mL) was refluxed overnight; the reaction mixture was cooled, and the solids were filtered off and rinsed with EtOAc. All liquids were combined and concentrated in vacuo. The resulting residue was partitioned between EtOAc and 2 M NaOH solution in a 500-mL separation funnel. The organic phase was subsequently washed with 1 M HCl, saturated NaCl solution, dried over sodium sulfate, and concentrated in vacuo to give the crude title compound (22.1 g) that was used in the next step without further purification. 1H NMR (200 MHz, CDCl3): δ (ppm)=7.7-6.6 (m, 12H), 5.08 (s, 2H).

Workup

  1. temperaturewas refluxed overnight
  2. temperaturethe reaction mixture was cooled
  3. filtrationthe solids were filtered off
  4. washrinsed with EtOAc
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was partitioned between EtOAc and 2 M NaOH solution in a 500-mL separation funnel
  7. washThe organic phase was subsequently washed with 1 M HCl, saturated NaCl solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5518f672060a445fb80dfba7e5250f97
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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