Benzyl 4-Hydroxybenzoate → Benzyl 4-n-dodecylcarbonyloxybenzoate

HRID 324148

Reaction equation

HRID 324148 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[CH:24]=[CH:23][C:12]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[CH:11][CH:10]=1.[C:25](Cl)(=[O:38])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C1(C)C=CC=CC=1>[CH2:26]([C:25]([O:8][C:9]1[CH:24]=[CH:23][C:12]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[CH:11][CH:10]=1)=[O:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 8471TriethylamineHCID 87288Tridecanoyl chloride

Product 1

HCID 22002898Benzyl 4-n-dodecylcarbonyloxybenzoateYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

{circle around (1)}: A solvent comprising 1.1 g of triethylamine and 5 g of toluene was added dropwise to a mixture comprising 2.28 g of benzyl 4-hydroxybenzoate, 2.33 g of n-tridecanoic chloride and 15 g of toluene in 30 minutes while cooling it with ice. After finishing adding dropwise, the mixture was stirred at room temperature for 3 hours. After finishing the reaction, deposited salts were filtered off, and the filtrate was neutralized with ½ N hydrochloric acid and washed with water. Then, toluene was distilled off under reduced pressure, and the resultant residue was recrystallized from ethanol, whereby 3.52 g of benzyl 4-n-dodecylcarbonyloxybenzoate was obtained in the form of a colorless crystal.

Workup

  1. temperaturewhile cooling it with ice
  2. additionAfter finishing adding dropwise
  3. customthe reaction
  4. filtrationwere filtered off
  5. washwashed with water
  6. distillationThen, toluene was distilled off under reduced pressure
  7. customthe resultant residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-5474de2af51041589549d0ca30e02ea1
Source dataset
uspto-grants-2001_04
Patent number
US06217793B1

Linked notes

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