[2-(2-Amino-4-chlorophenoxy)phenyl]methanol → [2-(2-Acetamido-4-chlorophenoxy)phenyl]methyl acetate

HRID 1973336Notes

Reaction equation

HRID 1973336 reaction equation
[NH2:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][OH:8]>N1C=CC=CC=1.C(OC(=O)C)(=O)C>[C:3]([O:8][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=1[O:4][C:3]1[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:2]=1[NH:1][C:7](=[O:8])[CH3:6])(=[O:4])[CH3:2]

Participants

4

Reactant 1

HCID 54153355[2-(2-Amino-4-chlorophenoxy)phenyl]methanol

Product 1

HCID 20357201[2-(2-Acetamido-4-chlorophenoxy)phenyl]methyl acetate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

0.026 Part of 2-(2-amino-4-chlorophenoxy)benzyl alcohol is dissolved in 0.5 part pyridine and 0.5 part by volume acetic anhydride and allowed to stand at room temperature for 16 hours. The solvent is removed by evaporation under a nitrogen atmosphere and the resultant residue chromatographed on 0.6 part silicic acid. Elution with a 5:95 mixture of ethyl acetate-benzene and recrystallization from a mixture of ethyl acetate and benzene affords 2-(2-acetamido-4-chlorophenoxy)benzyl acetate. This compound melts at about 83° - 84° C. and is represented by the following structural formula. ##STR6## Elemental analysis shows C, 61.71%; H, 5.30%; Cl, 10.73%; N, 4.01%. The calculated values are C, 61.17%; H, 4.83%, Cl, 10.62%; and N, 4.20%.

Workup

  1. customThe solvent is removed by evaporation under a nitrogen atmosphere
  2. customthe resultant residue chromatographed on 0.6 part silicic acid
  3. washElution
  4. additionwith a 5:95 mixture of ethyl acetate-benzene and recrystallization
  5. additionfrom a mixture of ethyl acetate and benzene

Sources & evidence

ORD record
ord-05ecc5afa10942f7bc4cff5f42b1befb
Source dataset
uspto-grants-1976_12
Patent number
US03997401

Reaction notes

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