4444-91-1

Basic information

• Product Name: 10-hydroxyoctadecan-9-one
• Synonyms: 10-hydroxyoctadecan-9-one;10-Hydroxy-9-octadecanone;Einecs 224-682-6
• CAS NO: 4444-91-1
• Molecular Formula: C₁₈H₃₆O₂
• Molecular Weight: 284.47724
• EINECS: 224-682-6
• Mol File: 4444-91-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 310.1°Cat760mmHg
• Flash Point: 131.2°C
• Appearance: /
• Density: 0.887g/cm³
• Vapor Pressure: 5.5E-05mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: 10-hydroxyoctadecan-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: 10-hydroxyoctadecan-9-one(4444-91-1)
• EPA Substance Registry System: 10-hydroxyoctadecan-9-one(4444-91-1)

Safety Data

• Hazardous Substances Data: 4444-91-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 3118, 1991 DOI: 10.1021/jo00009a035

InChI:InChI=1/C18H36O2/c1-3-5-7-9-11-13-15-17(19)18(20)16-14-12-10-8-6-4-2/h17,19H,3-16H2,1-2H3

Upstream product

• 764-85-2 Nonanoyl chloride 
• 56-23-5 tetrachloromethane 
• 1731-84-6 nonanoic acid methyl ester 
• 15962-87-5 octadecane-9,10-diol 
• 7297-29-2 methyl 9⁽¹⁰⁾-hydroxy 10⁽⁹⁾-oxo octadecanoate 
• 2566-91-8 epoxidized methyl oleate 
• 112-62-9 Methyl oleate 
• 217650-09-4 nonanoylzirconocene chloride 
• 27104-72-9 methyl isoquinoline-1-carboxylate 
• 96-34-4 methyl chloroacetate 
• 78-93-3 butanone 
• 124-19-6 nonan-1-al 
• 111-67-1 2-octene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 18394-00-8 9-octadecanone 
• 112-05-0 nonanoic acid 
• 124-19-6 nonan-1-al 

Relevant articles and documents

Reissert-type acylation with acylzirconocene chloride complexes

In the presence of ClCO2Et, the use of CuI in MeNO2 efficiently catalyzed the Reissert-type acylation of isoquinoline derivatives with acylzirconocene chlorides. In the reaction of quinolines with acylzirconocene chlorides, the choic

Homogeneous and heterogeneous catalytic (dehydrogenative) oxidation of oleochemical 1,2-diols to α-hydroxyketones

Herein, the preparation of methyl oleate α-hydroxyketone from the corresponding 1,2-diol was investigated using both homogeneous and heterogeneous systems. Homogeneous conditions using a Pd(OAc)2/neocuproine complex were first developed using oxygen as a sole oxidant under mild conditions (MeOH, 50 °C). Under these conditions, the conversion of diol reached 95%, and α-hydroxyketone was obtained with 97% selectivity. The access to α-hydroxyketone has also been studied by dehydrogenation using a range of heterogeneous catalysts under solvent-free conditions at high temperatures (160-180 °C). Dehydrogenation using activated Ru/C under vacuum provided α-hydroxyketone with 93% conversion and 82% GC yield. The optimized conditions were applied to a range of oleochemical diols, including a vegetable oil derivative, to obtain the corresponding α-hydroxyketones with up to 74% isolated yields.

Thiazolylidene-Catalyzed Cleavage of Methyl Oleate-Derived α-Hydroxy Ketone to the Corresponding Free Aldehydes

The thiazolylidene-catalyzed cleavage of the α-hydroxy ketone derived from methyl oleate gave the corresponding aldehydes under nonoxidative conditions through a retro-benzoin process. The aldehydes produced are in equilibrium with their corresponding acyloins. To illustrate the synthetic utility of this protocol, the aldehydes were recovered by distillation.