4-Aminophenol → 2-Cyclohexyl-N-(4-hydroxy-phenyl)-acetamide

HRID 1179659Notes

Reaction equation

HRID 1179659 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH:9]1([CH2:15][C:16](Cl)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.N1C=CC=CC=1>ClCCl>[CH:9]1([CH2:15][C:16]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 1049PyridineHCID 2757989Cyclohexylacetyl chloride

Product 1

HCID 220477802-Cyclohexyl-N-(4-hydroxy-phenyl)-acetamideYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-aminophenol (3.83 g, 35.1 mmol) in dichloromethane (50 ml) were added cyclohexylacetyl chloride (11.26 g, 70.1 mmol) and pyridine (5.67 ml, 70.1 mmol), while cooling the reaction mixture in an ice bath. After the addition was completed, the cooling bath was removed and stirring was continued overnight at room temperature. The solvent was removed and the residue was dissolved in THF (300 ml). 6N NaOH (aq, 41 ml) was added and the mixture was stirred at room temperature for 4 h. The solution was acidified with 1 N hydrochloric acid. The solvent was removed by evaporation. The solid material was collected by filtration, dried in vacuo at 40° C. and dissolved in methanol (100 ml). A solution of KOH (5.5 g) in methanol (50 ml) was added. After stirring for 1 h at room temperature water (200 ml) was added and the organic solvent was removed by evaporation. The aqueous phase was acidified with 1 N HCl. The solid material was isolated by filtration and dried in vacuo at 40° C. yielding the title compound (6.31 g, 77% yield, pink crystals).

Workup

  1. temperaturewhile cooling the reaction mixture in an ice bath
  2. additionAfter the addition
  3. customthe cooling bath was removed
  4. customThe solvent was removed
  5. dissolutionthe residue was dissolved in THF (300 ml)
  6. addition6N NaOH (aq, 41 ml) was added
  7. stirringthe mixture was stirred at room temperature for 4 h
  8. customThe solvent was removed by evaporation
  9. filtrationThe solid material was collected by filtration
  10. customdried in vacuo at 40° C.
  11. dissolutiondissolved in methanol (100 ml)
  12. additionA solution of KOH (5.5 g) in methanol (50 ml) was added
  13. stirringAfter stirring for 1 h at room temperature water (200 ml)
  14. additionwas added
  15. customthe organic solvent was removed by evaporation
  16. customThe solid material was isolated by filtration
  17. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-86ba96ca870c46158ee05c870b2e94a2
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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