4-Cyanophenol → HCID 11063427, compound

HRID 892540Notes

Reaction equation

HRID 892540 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].[OH-].[CH2:13]([N+](C)(C)C)[C:14]1[CH:19]=[CH:18]C=[CH:16][CH:15]=1>O.ClCCl>[CH2:19]([C:14]([CH3:13])([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:15]#[CH:16])[CH3:18]

Participants

6

Reactant 3

HCID 130194-CyanophenolHCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 11063427HCID 11063427, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

17.47 g of 2-chloro-2-methylpent-1-yne were added to a mixture of 11.9 g of 4-cyanophenol, 6.0 g of sodium hydroxide, 15 ml of a 40% methanolic solution of benzyltrimethylammonium hydroxide in 85 ml of water and 85 ml of dichloromethane and stirred for 4 days. The organic phase was separated, washed with 2M sodium hydroxide solution, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:9) for the elution to give 10.1 g of 4-(1-ethyl-1-methyl-2-propynyloxy)benzonitrile.

Workup

  1. customThe organic phase was separated
  2. washwashed with 2M sodium hydroxide solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-0145564f88e04d1f8f7749b8a3d1d027
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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