Dimethylformamide → HCID 14850627, compound

HRID 1074275Notes

Reaction equation

HRID 1074275 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1.[OH-].[Na+].CN(C)C=O>O>[C:11]([C:9]1[CH:8]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)[O:15][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 708253,5-Di-tert-butylphenolHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 14850627HCID 14850627, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5.1 g (25 mmole) of 3,5-di-t-butylphenol, 4.2 g (25 mmole) of alpha-bromo-p-tolunitrile, 1.0 g (25 mmole) sodium hydroxide and 75 ml of dimethylformamide was heated at 120° C. for about sixteen hours. The mixture was poured into 700 ml of water to give an oil which rapidly solidified. The solid was collected, rinsed with water, and recrystallized once from ethanol and twice from hexane to give 1.0 g of white crystalline 4-(3,5-di-t-butylphenoxymethyl)-1-benzenecarbonitrile, m.p. 118°-121° C. Analysis: Calculated for C22H27NO: %C, 82.2; %H, 8.5; %N, 4.4; Found: %C, 82.7; %H, 8.6; %N, 4.1.

Workup

  1. customto give an oil which
  2. customThe solid was collected
  3. washrinsed with water
  4. customrecrystallized once from ethanol and twice from hexane

Sources & evidence

ORD record
ord-98809a2100e84034a8b61e358929cf83
Source dataset
uspto-grants-1990_11
Patent number
US04973731

Reaction notes

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