Water → 2-Isopropoxy-4-methoxybenzonitrile

HRID 1582471Notes

Reaction equation

HRID 1582471 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11].I[CH:19]([CH3:21])[CH3:20].O>CC(C)=O>[CH:19]([O:7][C:8]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 114236802-Hydroxy-4-methoxybenzonitrile

Product 1

HCID 227210812-Isopropoxy-4-methoxybenzonitrileYield 87.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Cesium carbonate (51.5 g, 158 mmol) was added to a solution of 2-hydroxy-4-methoxybenzonitrile (11.8 g, 79 mmol) in acetone (100 mL). 2-Iodopropane (12.5 mL, 125 mmol) was added. The mixture was heated at reflux for 3 h. Water was added and the mixture was extracted with diethyl ether (4×100 mL). The combined organic extracts were washed with diluted ammonium hydroxide, brine and dried (MgSO4). Evaporation of the solvents and chromatography of the residue over silica gel using 5% diethyl ether in hexanes gave 2-isopropoxy-4-methoxybenzonitrile (13.2 g, 87%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. extractionthe mixture was extracted with diethyl ether (4×100 mL)
  4. washThe combined organic extracts were washed with diluted ammonium hydroxide, brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvents and chromatography of the residue over silica gel using 5% diethyl ether in hexanes

Sources & evidence

ORD record
ord-8fbdea1534744ad9b3c63b1d90baa6fc
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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