4-Chlorophenol → 4-Chlorophenyl 4-(8-cyclohexyloctylamino)benzoate

HRID 905273Notes

Reaction equation

HRID 905273 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[CH:17]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]2[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(Cl)Cl>[CH:17]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]2[CH:40]=[CH:39][C:35]([C:36]([O:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:37])=[CH:34][CH:33]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 8471TriethylamineHCID 20475769p-(8-Cyclohexyloctyl)aminobenzoyl chloride hydrochloride

Product 1

HCID 204758364-Chlorophenyl 4-(8-cyclohexyloctylamino)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6.4 g. 4-chlorophenol and 7.6 g. triethylamine in 500 ml. methylene chloride is added 10.4 g. 4-(8-cyclohexyloctylamino)benzoyl chloride hydrochloride in 250 ml. methylene chloride. After four hours at reflux, the solution is cooled, washed with water and dilute phosphoric acid, and dried. After passing the solution through a column of alumina, the solvent is evaporated an the residue is crystallized from diisopropyl ether.

Workup

  1. temperatureAfter four hours at reflux
  2. temperaturethe solution is cooled
  3. washwashed with water and dilute phosphoric acid
  4. customdried
  5. customthe solvent is evaporated an the residue
  6. customis crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-e23027eb14544ef0a5f2b75fae7a2471
Source dataset
uspto-grants-1983_12
Patent number
US04423051

Reaction notes

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