496-03-7

Basic information

• Product Name: 2-ethyl-3-hydroxyhexanal
• Synonyms: 2-ethyl-3-hydroxyhexanal;BUTYRALDOL;Butylaldol
• CAS NO: 496-03-7
• Molecular Formula: C₈H₁₆O₂
• Molecular Weight: 144.21144
• EINECS: 207-812-6
• Mol File: 496-03-7.mol

Chemical Properties

• Boiling Point: 216.9°Cat760mmHg
• Flash Point: 86.7°C
• Appearance: /
• Density: 0.923g/cm³
• Vapor Pressure: 0.0294mmHg at 25°C
• Refractive Index: 1.435
• PKA: 14.56±0.20(Predicted)
• CAS DataBase Reference: 2-ethyl-3-hydroxyhexanal(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ethyl-3-hydroxyhexanal(496-03-7)
• EPA Substance Registry System: 2-ethyl-3-hydroxyhexanal(496-03-7)

Safety Data

• Hazardous Substances Data: 496-03-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Ethyl-3-hydroxyhexanal is used as a key intermediate in the preparation of various organic compounds, such as 2-ethyl-2-hexenal, 2-ethylhexanol, 2-ethylhexanal, 2-ethylhexanoic acid, and 2-ethyl-1,3-hexanediol. These compounds find applications in different industries, including pharmaceuticals, fragrances, and flavorings.
Used in Aldol Condensation Reactions:
2-Ethyl-3-hydroxyhexanal is a reagent useful for the Aldol condensation reactions. The Aldol condensation is a fundamental organic reaction that involves the nucleophilic addition of an enolate ion to an aldehyde or ketone, resulting in the formation of a β-hydroxy aldehyde or ketone. This reaction is widely used in organic synthesis to form carbon-carbon bonds and construct complex molecular structures. The presence of the aldehyde group in 2-ethyl-3-hydroxyhexanal makes it a suitable reactant for the Aldol condensation, allowing the formation of new compounds with diverse functional groups and structural features.

Synthesis

2-Ethyl-3-hydroxyhexanal is prepared primarily by aldol condensation of butanal at 30℃ in the presence of an aqueous sodium hydroxide solution and a phase-transfer catalyst; the reaction is stopped by addition of acetic acid.

InChI:InChI=1/C8H16O2/c1-3-5-8(10)7(4-2)6-9/h6-8,10H,3-5H2,1-2H3

Upstream product

• 123-72-8 butyraldehyde 
• 109-89-7 diethylamine 
• 92954-34-2 2-allyl-1,3-dicyclohexylisourea 
• 2043-61-0 cyclohexanecarbaldehyde 
• 60-29-7 diethyl ether 
• 94-96-2 2-ethyl-1,3-hexane diol 
• 1066-30-4 chromium(lll) acetate 
• 64344-45-2 (E)-2-ethyl-2-hexenal 
• 67-64-1 acetone 
• 110-43-0 n-pentyl methyl ketone 
• 107-87-9 2-Pentanone 
• 75-87-6 chloral 
• 536-74-3 phenylacetylene 
• 123-19-3 4-heptanone 

Downstream Products

• 18618-91-2 3-(hydroxymethyl)heptan-4-yl butyrate 
• 10324-64-8 2-Ethylhexen-2-al-2,4-dinitrophenylhydrazon 
• 27122-56-1 2-Ethyl-1-phenyl-hexane-1,3-diol 
• 27122-53-8 5-ethyl-decane-4,6-diol 
• 645-62-5 2-ethylhexenal 
• 123-19-3 4-heptanone 
• 123-72-8 butyraldehyde 

Relevant articles and documents

Highly diastereoselective aldol reactions of 3-Fluorooxindoles promoted by MgBr2?OEt2/iPr2NEt

A highly diastereoselective aldol reaction between 3-fluorooxindoles and aromatic aldehydes has been developed. Commercially available, cheap Lewis acid MgBr2[rad]OEt2 was used to promote the reaction. The reaction has a broad substrate scope with respect to both 3-fluorooxindoles and aromatic aldehydes, giving a series of α-fluoro-β-hydroxyoxindoles in good yields with high diastereoselectivities (63–94 percent yield, up to 99:1 anti/syn).

Highly selective catalytic cross-aldol reactions of chloral with aliphatic aldehydes

An efficient synthetic method for β-trichloromethyl-β-hydroxy aldehydes is described. Using piperidine or L-prolinamide as the catalyst, direct cross-aldol reactions of chloral with aliphatic aldehydes occur smoothly at room temperature. The cross-aldol condensation products are isolated in high yields (up to 95%), and a moderate to high enantioselectivity (up to 88% ee) is observed in the case of L-prolinamide. Georg Thieme Verlag Stuttgart.

Aldol Addition of Butyraldehyde over Solid Base Catalysts

Aldol addition of butyraldehyde was investigated on alkaline earth oxides, zirconium oxide, and lanthanum oxide to compare the active site and mechanism with those for aldol addition of acetone.It is found that the active site is the surface O2(1-) and th

Development of an azanoradamantane-type nitroxyl radical catalyst for class-selective oxidation of alcohols

The development of 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO; 1,5-dimethyl-Nor-AZADO, 2) as an efficient catalyst for the selective oxidation of primary alcohols in the presence of secondary alcohols is described. The compact and rigid structure of the azanoradamantane nucleus confers potent catalytic ability to DMN-AZADO (2). A variety of hindered primary alcohols such as neopentyl primary alcohols were efficiently oxidized by DMN-AZADO (2) to the corresponding aldehydes, whereas secondary alcohols remained intact. DMN-AZADO (2) also has high catalytic efficiency for one-pot oxidation from primary alcohols to the corresponding carboxylic acids in the presence of secondary alcohols and for oxidative lactonization from diols.

9-azanoradamantane N—oxyl compound and method for producing same, and organic oxidation catalyst and method for oxidizing alcohols using 9-azanoradamantane N—oxyl compound

An organocatalyst for oxidizing alcohols in which a primary alcohol is selectively oxidized in a polyol substrate having a plurality of alcohols under environmentally-friendly conditions. The organic oxidation catalyst has an oxygen atom bonded to a nitrogen atom of an azanoradamantane skeleton and at least one alkyl group at positions 1 and 5. The oxidation catalyst has higher activity than TEMPO, which is an existing oxidation catalyst, in the selective oxidation reaction of primary alcohols, and better selectivity than AZADO and 1-Me-AZADO. This DMN-AZADO can be applied to the selective oxidation reaction of primary alcohols that contributes to shortening the synthesizing process for pharmaceuticals, pharmaceutical raw materials, agricultural chemicals, cosmetics, organic materials, and other such high value-added organic compounds.

Amino functionalized chitosan as a catalyst for selective solvent-free self-condensation of linear aldehydes

An aminopropyltrimethoxysilane functionalized chitosan was found to be an efficient solid base catalyst for the self-aldol condensation of linear aldehydes under solvent-free conditions. The modified catalyst was characterized using physical techniques, elemental analysis, FT-IR, and TGA. The modified chitosan was evaluated for the aldol condensation of C3-C7 linear aldehydes in which the selective formation was obtained for α,β-unsaturated aldehydes. A decreasing trend in the conversion from propanal to heptanal was observed. Propanal and pentanal were subjected for detail investigations to study the effect of parameters like amount of catalyst and aldehyde, and temperature on the conversion and selectivity. Kinetic performance of the modified chitosan investigated for a representative aldehyde, pentanal showed that the rate was increased with the catalyst amount, pentanal and temperature. The catalyst was reused up to six cycles without significant loss in its activity and selectivity.

The continuous self aldol condensation of propionaldehyde in supercritical carbon dioxide: A highly selective catalytic route to 2-methylpentenal

The aldol reactions of propionaldehyde and butyraldehyde have been explored in supercritical CO2, scCO2, using an automated continuous flow reactor. The reaction was found to proceed over a variety of heterogeneous acidic and basic catalysts and with increased selectivity compared to using neat reactants.

Processes for preparing beta-hydroxy-ketones and alpha,beta-unsaturated ketones

Processes for producing β-hydroxy-ketones and α,β-unsaturated ketones are disclosed which comprise the crossed condensation of an aldehyde with a ketone in the presence of a hydroxide or alkoxide of alkali metal or an alkaline earth metal as catalyst. The products of the process, β-hydroxy-ketones and α,β-unsaturated ketones, are useful for the preparation of many commercially important products in the chemical process industries including solvents, drug intermediates, flavors and fragrances, other specialty chemical intermediates.

InBr3-Et3N promoted alkynylation of aldehydes and N,O-acetals under mild conditions: Facile and simple preparation of propargylic alcohols and amines

The use of a novel InBr3-Et3N reagent system to promote addition reactions of 1-alkynes not only with a variety of aromatic or bulky aliphatic aldehydes but also with N,O-acetals is described. The corresponding propargylic alcohols or amines are produced in good to excellent yields.

COMPOUNDS FOR THE CONTROLLED RELEASE OF ACTIVE ALDEHYDES

The present invention relates to the field of perfumery. More particularly, it concerns an aldoxane derivative of Formula (I) capable of protecting an active aldehyde R1CHO, for example a perfumery or flavor aldehyde, from a chemically aggressive medium into which they have to be added, and then of releasing said active aldehyde at the desired moment. The present invention concerns also the use of said compound in perfumery or in the flavor industry as well as the compositions or articles associated with said aldoxanes.