Guaiacol → 4-[5-(2-Methoxyphenoxy)pentoxy]benzonitrile

HRID 6070

Reaction equation

HRID 6070 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].[H-].[Na+].[H][H].I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1>CN(C=O)C.O>[CH3:9][O:8][C:1]1[CH:7]=[CH:6][CH:5]=[CH:4][C:2]=1[O:3][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 460GuaiacolHCID 24758Sodium hydrideHCID 16202445Benzonitrile, 4-[(5-iodopentyl)oxy]-HCID 178418361HCID 178418361, compound

Product 1

HCID 197948854-[5-(2-Methoxyphenoxy)pentoxy]benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5.1 g (41 mmol) of guaiacol in 41 mL of DMF, cooled in an icebath, is added in portions, 20 g (41 mmole) of sodium hydride (50% dispersion in oil). The reaction is allowed to warm up to room temperature and stirred until no further hydrogen evolution is observed. The solution is then again cooled in an ice-bath and a solution of 13 g (41 mmol) 4-(5-iodopentoxy) benzonitrile in 82 mL DMF added. The reaction is allowed to warm up to room temperature and stirred for 18 h before pouring the mixture into water. The resulting solid is filtered off and dried to give 4-[5-(2-methoxyphenoxy)pentoxy] benzonitrile, m.p. 61°-63° C.

Workup

  1. temperatureThe solution is then again cooled in an ice-bath
  2. temperatureto warm up to room temperature
  3. filtrationThe resulting solid is filtered off
  4. customdried

Sources & evidence

ORD record
ord-fdd2eb38b67e4d6b8e06115e859cab46
Source dataset
uspto-grants-1993_09
Patent number
US05246965

Linked notes

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