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Cas Database

91119-04-9

91119-04-9

Identification

  • Product Name:5-(2-phenylethyl)-5-nonanol

  • CAS Number: 91119-04-9

  • EINECS:

  • Molecular Weight:248.409

  • Molecular Formula: C17H28O

  • HS Code:

  • Mol File:91119-04-9.mol

Synonyms:5-(2-phenylethyl)-5-nonanol

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Relevant articles and documentsAll total 4 Articles be found

A ONE-STEP CONVERSION OF ESTERS TO SECONDARY ALCOHOLS WITH LiBH4-RMgX

Comins, Daniel L.,Herrick, James J.

, p. 1321 - 1324 (1984)

A one-pot synthesis of secondary alcohols from esters and LiBH4-RMgX is described.

A new synthetic method for methyl ketones from carboxylic acids using metallic strontium and methyl iodide

Miyoshi, Norikazu,Matsuo, Tsuyoshi,Asaoka, Masashi,Matsui, Aki,Wada, Makoto

, p. 28 - 29 (2007/10/03)

Carboxylic acids reacted with metallic strontium and methyl iodide to give methyl ketones preferentially in moderate to good yields. Copyright

Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes

Nudelman,Garcia

, p. 1387 - 1394 (2007/10/03)

A tandem reaction between (E)-cinnamaldehyde, 1a, and phenyllithium affording β-substituted dihydrochalcones was recently reported. NMR spectroscopic studies on the reaction mixture, as well as isotopic exchange reactions and trapping of two intermediates, provide clues on the several mechanistic steps of this new reaction. Extended studies revealed that β-alkyl-substituted α,β-unsaturated aldehydes and aliphatic lithium reagents did not afford good yields of the tandem reaction products, while aromatic lithium reagents gave good results. The aggregation features of the aryllithium reagents and the extended charged delocalization effects are considered to promote β-selectivity. This approach provides a convenient route for the synthesis of a wide variety of β-alkyl-substituted dihydrochalcones.

On the Preparation of N-Acylpyrroles and their Use in the Synthesis of Ketones

Brandaenge, Svante,Holmgren, Erik,Leijonmarck, Hans,Rodriguez, Benito

, p. 922 - 928 (2007/10/03)

Two methods for the preparation of N-acylpyrroles have been studied: (a) the reaction between pyrrole and N-acylimidazoles and (b) the oxidation of amides of 3-pyrroline.The reactions between N-acylpyrroles and organolithium compounds can be directed to give ketones in good yields.The initially formed tetrahedral intermediates in these reactions are relatively stable and pyrrolylcarbinols are isolable intermediates.A Reformatsky-Claisen type ring-closure gave a more than doubled yield when an N-acylpyrrole group was used as an electrophile instead of an ester group; the increased stability of the initially formed tetrahedral intermediate presumably accounts for the observed results.

Process route upstream and downstream products

Process route

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

butyl magnesium bromide
693-04-9

butyl magnesium bromide

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

1-phenylheptan-3-ol
19969-03-0

1-phenylheptan-3-ol

5-(2-phenylethyl)-5-nonanol
91119-04-9

5-(2-phenylethyl)-5-nonanol

Conditions
Conditions Yield
With lithium borohydride; In tetrahydrofuran; at -20 ℃; for 24h; Yield given. Yields of byproduct given;
1-iodo-butane
542-69-8

1-iodo-butane

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

1-phenyl-heptan-3-one
19969-04-1

1-phenyl-heptan-3-one

5-(2-phenylethyl)-5-nonanol
91119-04-9

5-(2-phenylethyl)-5-nonanol

Conditions
Conditions Yield
With strontium; In tetrahydrofuran; at 20 ℃; for 0.5h;
1-(3-phenylpropanoyl)-2,5-dihydropyrrole
173549-40-1

1-(3-phenylpropanoyl)-2,5-dihydropyrrole

5-(2-phenylethyl)-5-nonanol
91119-04-9

5-(2-phenylethyl)-5-nonanol

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 94 percent / DDQ / ethyl acetate / 5 h / Heating
2: tetrahydrofuran; hexane / 0.5 h / -78 °C
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; ethyl acetate;
n-butyllithium
109-72-8,29786-93-4

n-butyllithium

3-phenyl-1-(1H-pyrrol-1-yl)propan-1-one
112448-69-8

3-phenyl-1-(1H-pyrrol-1-yl)propan-1-one

1-phenyl-heptan-3-one
19969-04-1

1-phenyl-heptan-3-one

5-(2-phenylethyl)-5-nonanol
91119-04-9

5-(2-phenylethyl)-5-nonanol

1-phenyl-3-(1-pyrrolyl)-3-heptanol
173549-44-5

1-phenyl-3-(1-pyrrolyl)-3-heptanol

Conditions
Conditions Yield
In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Yields of byproduct given;
In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Yield given;
n-butyl magnesium bromide
693-03-8

n-butyl magnesium bromide

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

5-(2-phenylethyl)-5-nonanol
91119-04-9

5-(2-phenylethyl)-5-nonanol

Conditions
Conditions Yield
With diethyl ether;
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

n-butyllithium
109-72-8,29786-93-4

n-butyllithium

(1E)-1-phenylhept-1-en-3-ol
109801-00-5

(1E)-1-phenylhept-1-en-3-ol

(E)-1-phenylhept-1-en-3-one
19184-21-5,4071-84-5,41903-83-7

(E)-1-phenylhept-1-en-3-one

5-(2-phenylethyl)-5-nonanol
91119-04-9

5-(2-phenylethyl)-5-nonanol

Conditions
Conditions Yield
In tetrahydrofuran; at 20 ℃; for 2h; Further Variations:; Temperatures; reaction times; Product distribution;
45 % Chromat.
8 % Chromat.
5 % Chromat.
n-butyllithium
109-72-8,29786-93-4

n-butyllithium

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

5-(2-phenylethyl)-5-nonanol
91119-04-9

5-(2-phenylethyl)-5-nonanol

Conditions
Conditions Yield
ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

butyl magnesium bromide
693-04-9

butyl magnesium bromide

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

1-phenylheptan-3-ol
19969-03-0

1-phenylheptan-3-ol

5-(2-phenylethyl)-5-nonanol
91119-04-9

5-(2-phenylethyl)-5-nonanol

Conditions
Conditions Yield
With lithium borohydride; In tetrahydrofuran; at -20 ℃; for 24h; Yield given. Yields of byproduct given;
1-iodo-butane
542-69-8

1-iodo-butane

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

1-phenyl-heptan-3-one
19969-04-1

1-phenyl-heptan-3-one

5-(2-phenylethyl)-5-nonanol
91119-04-9

5-(2-phenylethyl)-5-nonanol

Conditions
Conditions Yield
With strontium; In tetrahydrofuran; at 20 ℃; for 0.5h;
1-(3-phenylpropanoyl)-2,5-dihydropyrrole
173549-40-1

1-(3-phenylpropanoyl)-2,5-dihydropyrrole

5-(2-phenylethyl)-5-nonanol
91119-04-9

5-(2-phenylethyl)-5-nonanol

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 94 percent / DDQ / ethyl acetate / 5 h / Heating
2: tetrahydrofuran; hexane / 0.5 h / -78 °C
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; ethyl acetate;

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