Benzyl Alcohol → Benzyl caprate

反応式

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

参加物

反応物 4

HCID 244Benzyl Alcohol

HCID 962Water

HCID 8471Triethylamine

HCID 10928Ethyl chloroformate

生成物 2

HCID 2969Decanoic Acid

HCID 562246Benzyl caprate収率 99%

実験手順

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.