4-Chlorophenol → 4-Chlorophenyl 2-(4-tetradecenylamino)benzoate

HRID 325567Notes

Reaction equation

HRID 325567 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:31][C:32]1[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=1[C:34](Cl)=[O:35])[CH2:18][CH2:19][CH:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C(Cl)Cl>[CH2:17]([NH:31][C:32]1[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=1[C:34]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:35])[CH2:18][CH2:19][CH:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 8471TriethylamineHCID 737080852-(4-Tetradecenylamino)benzoyl chloride hydrochloride

Product 1

HCID 540889394-Chlorophenyl 2-(4-tetradecenylamino)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. 2-(4-tetradecenylamino)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-22e4cd2be3554b4c933f27f4dd7ff082
Source dataset
uspto-grants-1984_04
Patent number
US04440940

Reaction notes

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