Ethanol → 4-Chloro-5-(ethylamino)-2-methylphenol

HRID 1110647Notes

Reaction equation

HRID 1110647 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[CH2:11](I)[CH3:12].C(=O)([O-])O.[Na+].C(O)C>O>[CH3:10][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([NH:8][CH2:11][CH3:12])=[CH:6][C:5]=1[OH:9]

Participants

6

Reactant 4

HCID 702EthanolHCID 6340IodoethaneHCID 516892Sodium Bicarbonate2×HCID 101762415-Amino-4-chloro-o-cresol

Product 1

HCID 137964154-Chloro-5-(ethylamino)-2-methylphenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3 g of 4-chloro-2-methyl-5-aminophenol (0.016 mol), 2.6 g of ethyliodide (0.017 mol), 1.35 g of sodium hydrogen carbonate (0.016 mol) and 30 ml of ethanol was refluxed for 7 hours. After cooling and dilution with 50 ml of water, the solution was neutralized with a sodium hydrogen carbonate solution and then extracted three times with 50 ml of ethylacetate. The extract was dried over sodium sulfate and concentrated to dryness. The residue was recrystallized from toluene. Beige crystals melting at 205° C. were obtained.

Workup

  1. temperaturewas refluxed for 7 hours
  2. temperatureAfter cooling
  3. extractionextracted three times with 50 ml of ethylacetate
  4. dry with materialThe extract was dried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-e37002ee09054b418ccc239f6988a117
Source dataset
uspto-grants-1990_12
Patent number
US04976742

Reaction notes

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