Phosphorus oxychloride → 2-Hydroxy-3,5-diisopropyl benzonitrile

HRID 1272265Notes

Reaction equation

HRID 1272265 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6]([C:9]1[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[CH:15]=[C:11]([C:12]([NH2:14])=O)[C:10]=1[OH:21])([CH3:8])[CH3:7]>N1C=CC=CC=1>[OH:21][C:10]1[C:9]([CH:6]([CH3:7])[CH3:8])=[CH:17][C:16]([CH:18]([CH3:20])[CH3:19])=[CH:15][C:11]=1[C:12]#[N:14]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 184569023,5-Diisopropyl salicylamide

Product 1

HCID 184569012-Hydroxy-3,5-diisopropyl benzonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of phosphorous oxychloride (1.35 g, 8.8 mmole) and dry pyridine (12 mL) cooled to 0° C., a solution of 3,5-diisopropyl salicylamide (1.10 g, 5 mmole) and dry pyridine (5 mL) was slowly added drop by drop. The reaction mixture was stirred at room temperature, whereat the colour changed from colourless over violet to red. After extraction with ethyl acetate and washing with a saturated sodium chloride solution and 2N hydrochloric acid, the organic layer was dried and evaporated under reduced pressure. The obtained solid residue was recrystallized from acetonitrile, whereat there were obtained 610 mg (60%) of 2-hydroxy-3,5-diisopropyl benzonitrile.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washwashing with a saturated sodium chloride solution and 2N hydrochloric acid
  3. customthe organic layer was dried
  4. customevaporated under reduced pressure
  5. customThe obtained solid residue was recrystallized from acetonitrile, whereat there

Sources & evidence

ORD record
ord-42dfc3c4923e4cdcac231d2c808bdb1e
Source dataset
uspto-grants-2007_04
Patent number
US07208518B2

Reaction notes

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