Benzyl Alcohol → Benzyl decanoate

HRID 868661Notes

Reaction equation

HRID 868661 reaction equation
C(N([CH2:6][CH3:7])CC)C.Cl[C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH2:22]>>[C:12]([OH:22])(=[O:11])[CH2:13][CH2:19][CH2:20][CH2:15][CH2:16][CH2:17][CH2:18][CH2:6][CH3:7].[CH2:12]([O:11][C:9](=[O:10])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:15][CH2:14][CH2:6][CH3:7])[C:13]1[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 2

HCID 2969Decanoic AcidHCID 562246Benzyl decanoateYield 99%

Procedure

A solution of 1.722 g. (0.01 mole) of decanoic acid and 1.5 ml triethylamine in 25 ml water was prepared by warming on a water bath. The solution was rapidly cooled in an ice-salt bath while stirring. After the temperature of about -2° C. was reached, 1.0 ml. ethyl chloroformate was slowly added along with about 2 g. of crushed ice. Stirring was continuted for an additional hour (internal temperature was maintained) between 0 and -2° C.). Finally 1.5 ml. benzyl alcohol was added. Stirring of the reaction mixture was continued for 1/2 hour on a 60° water bath. After cooling, the ester was extracted twice by 30 ml ether, washed with sodium, bicarbonate solution then with water. After drying and evaporation of the solvent, the ester was distilled under reduced pressure to give 2.574 g. (99% yield) of benzyldecanoate. B.P. 208-210/15 mm. Anal. Calcd. for C17H26O2 :c, 77.82; H, 9.98. Found: C, 77.69; H, 10.03.

Workup

  1. temperatureby warming on a water bath
  2. temperatureThe solution was rapidly cooled in an ice-salt bath
  3. customAfter the temperature of about -2° C.
  4. stirringStirring
  5. waitwas continuted for an additional hour
  6. temperature(internal temperature was maintained) between 0 and -2° C.)
  7. stirringStirring of the reaction mixture
  8. temperatureAfter cooling
  9. extractionthe ester was extracted twice by 30 ml ether
  10. washwashed with sodium, bicarbonate solution
  11. customAfter drying
  12. customevaporation of the solvent
  13. distillationthe ester was distilled under reduced pressure
  14. customto give 2.574 g

Sources & evidence

ORD record
ord-3b9e6a5f0a2842ce8b3a71762b0bdf01
Source dataset
uspto-grants-1988_10
Patent number
US04780542

Reaction notes

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