4-Chlorophenol → 4-Chlorophenyl 4-(hexadecylamino)benzoate

HRID 1680294Notes

Reaction equation

HRID 1680294 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.[CH2:17]([NH:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C(Cl)Cl>[CH2:17]([NH:33][C:34]1[CH:35]=[CH:36][C:37]([C:38]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:39])=[CH:41][CH:42]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 8471TriethylamineHCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 234577774-Chlorophenyl 4-(hexadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6.4 g. (50 m moles) 4-chlorophenol and 7.6 g. (75 m moles) triethylamine in 500 ml. methylene chloride is added 10.4 g. (25 m moles) 4-(hexadecylamino)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 and 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
  6. customthe residue is crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-2102fa1351e64616bfc0751ae4653970
Source dataset
uspto-grants-1981_06
Patent number
US04272546

Reaction notes

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