Pyridine → 2-(Dodecanoyloxy)ethyl benzoate

HRID 616450Notes

Reaction equation

HRID 616450 reaction equation
[C:1]([O:9][CH2:10][CH2:11][OH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:19](Cl)(=[O:31])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C1C=CC=CC=1>[C:19]([O:12][CH2:11][CH2:10][O:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:31])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8166Dodecanoyl chloride2×HCID 66747Ethylene glycol monobenzoate

Product 1

HCID 203139472-(Dodecanoyloxy)ethyl benzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To sixteen grams (0.1 mole) of ethylene glycol monobenzoate containing 20 gms (0.25 mole) of pyridine was added 22 gms (0.1 mole) of lauroyl chloride with stirring. With the final addition of lauroyl chloride approximately 50 ml of benzene was added and the mixture stirred for 1 hour. The pyridine hydrochloride was filtered off and the product water washed to remove residual pyridine. The benzene solution was dried over anhydrous sodium sulfate and percolated through a column filled with activated alumina to removal residual free acid. The solvent was removed at reduced pressure. The product, 2-benzoyloxyethyl laurate, was characterized on the basis of the chemical shifts in the NMR spectrum and the absence of OH-stretching and other bands associated with reaction byproducts or impurities.

Workup

  1. additionwas added
  2. stirringthe mixture stirred for 1 hour
  3. filtrationThe pyridine hydrochloride was filtered off
  4. washthe product water washed
  5. customto remove residual pyridine
  6. dry with materialThe benzene solution was dried over anhydrous sodium sulfate
  7. additionfilled with activated alumina to removal residual free acid
  8. customThe solvent was removed at reduced pressure
  9. customother bands associated with reaction byproducts or impurities

Sources & evidence

ORD record
ord-e02536fae9a942e692408d42d6c13646
Source dataset
uspto-grants-1978_02
Patent number
US04074058

Reaction notes

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