1-Pentanol → 3-Methoxy-6-(2',6'-dimethylanilino)toluene

HRID 1165420Notes

Reaction equation

HRID 1165420 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:13])[C:6]([NH:9]C(=O)C)=[CH:7][CH:8]=1.Br[C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:22].C(=O)([O-])[O-].[K+].[K+].[OH-].[K+].CCCCCO>[Cu]I>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:13])[C:6]([NH:9][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:22])=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 62761-PentanolHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 684712-Bromo-m-xyleneHCID 95082N-(4-Methoxy-2-methylphenyl)-acetamide

Product 1

HCID 108576333-Methoxy-6-(2',6'-dimethylanilino)tolueneYield 28.6%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

A mixture of 14.3 g of 3-methoxy-6-acetylaminotoluene, 17.8 g of 2-bromo-m-xylene, 6.6 g of potassium carbonate, and 0.3 g of copper (I) iodide was stirred for 42 hours at 160°-210° C. After the reaction mixture was cooled, 22.9 g of potassium hydroxide and 66 ml of n-amyl alcohol were added to the mixture, which was then refluxed for 3.5 hours. Then the reaction mixture was cooled and washed with hot water. The n-amyl alcohol was removed by distillation, and the remaining reaction mixture was distilled under reduced pressure to obtain 5.5 g (28 percent of theoretical yield) of 3-methoxy-6-(2',6'-dimethylanilino)toluene.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. temperaturewas then refluxed for 3.5 hours
  3. temperatureThen the reaction mixture was cooled
  4. washwashed with hot water
  5. customThe n-amyl alcohol was removed by distillation
  6. customthe remaining reaction mixture
  7. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-00928abcfcc74f39a0b45cc959fa07e8
Source dataset
uspto-grants-1990_03
Patent number
US04910183

Reaction notes

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