Organophosphorus compounds. XII. A new synthesis of phosphindolines and phosphindoles

1974 ◽  
Vol 27 (4) ◽  
pp. 831 ◽  
Author(s):  
DJ Collins ◽  
LE Rowley ◽  
JM Swan
Keyword(s):  
Hydrochloric Acid ◽  
Zinc Chloride ◽  
Organophosphorus Compounds ◽  
Magnesium Bromide ◽  
New Synthesis

The reaction of 2-phenylethylphosphonous dichloride with zinc chloride at 170� followed by hydrolysis with concentrated hydrochloric acid, and oxidation, gave 72% of 1-hydroxyphosphindoline 1-oxide. Treatment of the derived phosphinic chloride with vinyl magnesium bromide at -40� afforded 1-vinylphosphindoline 1-oxide which underwent addition of dimethylamine to yield 1-(2'-dimethylaminoethyl)phosphindoline 1-oxide. The conversions of 1-chlorophosphindoline 1-oxide into 1-ethyl- and 1-phenyl-phosphindoline 1-oxide are described. Bromination of l-methoxy- phosphindoline 1-oxide with N-bromosuccinimide followed by dehydrobromination afforded 1-methoxyphosphindole 1-oxide. 1-(2'-Dimethylaminoethyl)phosphindoline 1-oxide and the corresponding phosphine sulphide were assayed for analgetic activity.

Organophosphorus compounds. X. A new synthesis of 1,2,3,4-tetrahydrophosphinolines

1974 ◽  
Vol 27 (4) ◽  
pp. 801 ◽  
Author(s):  
LE Rowley ◽  
JM Swan
Keyword(s):  
Hydrochloric Acid ◽  
Thionyl Chloride ◽  
Zinc Chloride ◽  
Grignard Reagent ◽  
Organophosphorus Compounds ◽  
Catalytic Amount ◽  
Ethyl Esters ◽  
Aluminium Chloride ◽  
Small Scale ◽  
New Synthesis

A new synthesis of the 1,2,3,4-tetrahydrophosphinoline ring is described. Reaction of 3-phenyl- propylphosphonous dichloride with zinc chloride at 170� followed by hydrolysis with hot concentrated hydrochloric acid, then oxidation with bromine, gave 91% of 1-hydroxy-1,2,3,4-tetrahydrophosphinoline 1-oxide (20b). Under conditions where oxidation was incomplete, 1,2,3,4-tetrahydrophosphinoline 1-oxide was isolated. On a small scale the reaction of 3-phenylpropylphosphonous dichloride with a catalytic amount of aluminium chloride at 220� gave 60% of l-chloro- 1,2,3,4-tetrahydrophosphinoline (18). Treatment of (20b) with thionyl chloride gave 1-chloro-1,2,3,4-tetrahydrophosphinoline 1-oxide which, upon reaction with the appropriate Grignard reagent, afforded 1-ethyl or 1-phenyl-1,2,3,4- tetrahydrophosphinoline 1-oxide. 1-Ethyl-1,2,3,4-tetrahydrophosphinoline 1-oxide was reduced with trichlorosilane to the phosphine, which upon reaction with sulphur yielded the corresponding phosphine sulphide. The methyl and ethyl esters of (20b) are described.

Extraction of β-Sitosterol from Jatropha Seed Oil

2011 ◽  
Vol 233-235 ◽  
pp. 1210-1213 ◽  
Author(s):  
Shu Yu Liu ◽  
Hao Lu ◽  
Li Jie Sun ◽  
Xin Guo
Keyword(s):  
Solvent Extraction ◽  
Hydrochloric Acid ◽  
Zinc Chloride ◽  
Seed Oil ◽  
Extraction Technique ◽  
Power Ratio ◽  
Optimum Conditions ◽  
Jatropha Seed ◽  
Solvent Extraction Technique

Solvent extraction technique was applied for the extraction of β-Sitosterol from jatropha seed oil．The optimum conditions for the lab scale extraction were obtained at 30ml solvent, 0.05g magnesium power, ratio of hydrochloric acid to zinc chloride of 1/1.75 (ml/g) and tetrahydrofuran as a solvent. Under the optical conditions, the yield of β-sitosterol was up to 3.27mg/g.

O-Benzylidene Derivatives of D-Arabinose Diethyl and Dipropyl Dithioacetal

1996 ◽  
Vol 49 (3) ◽  
pp. 273 ◽  
Author(s):  
J Kuszmann ◽  
E Gacsbaitz
Keyword(s):  
Hydrochloric Acid ◽  
Zinc Chloride ◽  
Partial Hydrolysis ◽  
Kinetic Control ◽  
Toluenesulfonic Acid ◽  
Thermodynamic Phase ◽  
Hydrolysis Of ◽  
Derivatives Of

Benzylidenation of D-arabinose diethyl and dipropyl dithioacetals with α,α-dimethoxytoluene in the presence of p-toluenesulfonic acid has been studied in detail. Under kinetic control the two terminal dioxolan -type 4,5-O-(R)- and 4,5-O-(S)-benzylidene diastereomers are formed first which are in equilibrium with each other In the thermodynamic phase of the reaction the corresponding dioxan -type 3,5-O-(R)- benzylidene isomer is formed too, but all three monobenzylidene isomers are gradually converted into the four possible dioxolan -type 2,3 : 4,5-di-O benzylidene diastereomers . The dioxan -type 2,4:3,5-di-O-benzylidene isomer was present only in trace amounts. When benzaldehyde was used as reagent in the presence of hydrochloric acid or zinc chloride only the 2,3: 4,5-di-O-benzylidene diastereomers were formed. Partial hydrolysis of the dibenzylidene derivatives yielded the corresponding 2,3-O-benzylidene diastereomers. Structures, including the chirality of the benzylidene groups, were determined by n.m.r. spectroscopy. A mechanism suggested for the reaction was partially supported by equilibration studies.

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