Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 29826-00-4

HRID 2210857ノート

反応式

HRID 2210857 の反応式
[CH:1](=O)/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OC)=O.CCCCCC.[C:44]([O:47]CC)(=[O:46])[CH3:45]>C(Cl)Cl>[C:44]([OH:47])(=[O:46])/[CH:45]=[CH:1]/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

参加物

5

反応物 3

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 5283361(E)-Dodec-2-en-1-alHCID 21226206Ethyl acetate hexane

生成物 1

HCID 531240429826-00-4

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To trans-2-dodecenal (4.5 g) dissolved in methylene chloride (80 ml) was added (carbomethoxymethylene)triphenylphosphorane (8.3 g), and the mixture was stirred for 2 hours. The reaction mixture was subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to 20:1) to give the methyl ester of trans,trans-2,4-tetradecadienoic acid (5.4 g). Potassium hydroxide (6.5 g) was dissolved in a mixed solvent of ethanol-water (1:1) (100 ml). The methyl ester of trans,trans-2,4-tetradecadienoic acid (5.4 g) was added to the mixture, and the resulting mixture was stirred at 60° C. for 40 minutes. After the reaction mixture was cooled, it was adjusted to the weak acidic range of pH with citric acid and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated to give trans,trans-2,4-tetradecadienoic acid (4.4 g). Hereafter, the title compound can be synthesized by the two methods described below.

出典と根拠

ORDレコード
ord-0a9891fe29b14a84b4c43b2757dac4ef
出典データセット
uspto-grants-1995_10
特許番号
US05461036

反応ノート

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