13851-11-1

Basic information

• Product Name: FENCHYL ACETATE
• Synonyms: FENCHYL ACETATE 96+% MIXTURE OF ALPHA&;FENCHYL ACETATE 90%;1,3,3-TRIMETHYL-2-NORBONYLACETATE;3,3-Dimethyl-8,9-dinorbornan-2-ylacetat;FENCHYLACETAT MIN. 95 P.;1,3,3-triMethylbicyclo[2.2.1]heptan-2-yl acetate;Fenchyl acetate, mixture of α- and β- ;1,3,3-trimethyl-2-norbornanoacetate
• CAS NO: 13851-11-1
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• EINECS: 237-588-5
• Mol File: 13851-11-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 220 °C(lit.)
• Flash Point: 168 °F
• Appearance: /
• Density: 0.98 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.117mmHg at 25°C
• Refractive Index: n20/D 1.456(lit.)
• CAS DataBase Reference: FENCHYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: FENCHYL ACETATE(13851-11-1)
• EPA Substance Registry System: FENCHYL ACETATE(13851-11-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: RB7660000
• Hazardous Substances Data: 13851-11-1(Hazardous Substances Data)

Usage

Chemical Properties

Fenchyl acetate has a mild, sweet odor reminiscent of fr oil.

Occurrence

Reported found in the oil from leaves and terminal branches of Juniperus rigida; in Seseli sibiricum; rosemary oil; fennel oil; oil of hinoki leaves Also reported found in ginger, Ocimum basilicum and mastic gum leaf oil

Preparation

By esterifcation of fenchyl alcohol with acetic anhydride in pyridine.

InChI:InChI=1/C12H20O2/c1-8(13)14-10-11(2,3)9-5-6-12(10,4)7-9/h9-10H,5-7H2,1-4H3

Synthetic route

Beta-pinene (177698-19-0) + acetic acid (64-19-7) → α-fenchyl acetate (13851-11-1)

Conditions	Yield
With PPA

Pinene (80-56-8, 177698-18-9) + acetic acid (64-19-7) → α-fenchyl acetate (13851-11-1)

Conditions	Yield
With PPA

acetic anhydride (108-24-7) + dl-fenchyl alcohol → α-fenchyl acetate (13851-11-1)

Conditions	Yield
acetic acid dl-fenchyl ester;

acetic anhydride (108-24-7) + Ld"-fenchyl alcohol → α-fenchyl acetate (13851-11-1)

Conditions	Yield
acetic acid Ld"-fenchyl ester;

Pinene (80-56-8, 177698-18-9) + acetic acid (64-19-7) → α-fenchyl acetate (13851-11-1) + isobornyl acetate (76-49-3, 125-12-2, 5655-61-8, 6626-35-3, 17283-45-3, 20347-65-3, 28974-17-6, 36386-52-4, 71424-71-0, 92618-89-8) + limonene. (138-86-3)

Conditions	Yield
With oxygen In water at 100℃; under 15001.5 Torr; for 10h; Inert atmosphere;

Pinene (80-56-8, 177698-18-9) + acetic acid (64-19-7) → Terpinolene (586-62-9) + α-fenchyl acetate (13851-11-1) + camphene (79-92-5) + endo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl acetate (76-49-3) + limonene. (138-86-3)

Conditions	Yield
at 150℃; under 4500.45 Torr; Reagent/catalyst; Microwave irradiation;

Pinene (80-56-8, 177698-18-9) + acetic acid (64-19-7) → Terpinolene (586-62-9) + α-fenchyl acetate (13851-11-1) + camphene (79-92-5) + endo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl acetate (76-49-3) + terpinyl acetate (80-26-2) + limonene. (138-86-3)

Conditions	Yield
With triacetoxyborane at 150℃; under 4500.45 Torr; Microwave irradiation;

Pinene (80-56-8, 177698-18-9) + acetic anhydride (108-24-7) → α-fenchyl acetate (13851-11-1) + terpinyl acetate (80-26-2) + isobornyl acetate (76-49-3, 125-12-2, 5655-61-8, 6626-35-3, 17283-45-3, 20347-65-3, 28974-17-6, 36386-52-4, 71424-71-0, 92618-89-8)

Conditions	Yield
With water In dichloromethane at 40℃; for 4h; Catalytic behavior; Temperature; Reagent/catalyst;	A n/a B 52.83 %Spectr. C n/a

Upstream product

• 80-56-8 Pinene 
• 108-24-7 acetic anhydride 
• 36386-49-9 fenchol 
• 64-19-7 acetic acid 
• 13293-47-5 2αH-pinan-3α-ylamine 
• 4695-62-9 Fenchol 
• 5813-49-0 nitrosyl acetate 
• 177698-19-0 Beta-pinene 

Relevant articles and documents

Solvent-free Acetylation Procedure

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Microwave-assisted α-pinene acidic catalytic isomerisation

A comparative study of microwave assisted α-pinene acidic catalytic isomerisation reactions with near-critical water procedure under microwave irradiation is presented. This study can be performed because in both cases the mechanism is similar, namely an acidiccatalyzed rearrangement. The non-critical method technique is milder using a lower temperature and pressure and a shorter reaction time than near-critical water conditions. The general aspect of the selectivity of the reaction products is changed, being higher for α-terpinolene and γ-terpinolene and lower for limonene and camphene compared to the non-critical conditions.

1,3,3-Trimethylbicyclo[2.2.1]heptan-2-endo-ol in Nucleophilic Substitution Reactions

1,3,3-Trimethylbicyclo[2.2.1]heptan-2-endo-ol (fenchol) reacts with acetonitrile in the presence of sulfuric acid to selectively form an isofenchane derivative - N-acetyl-1,5,5-trimethylbicyclo[2.2.1]heptan-2-exo-amine as a result of nucleophilic addition at the most accessible carbon atom of a nonclassical 1,3,3-trimethylbicyclo[2.2.1]heptyl cation. The H2SO4-catalyzed reaction with acetic acid results in exclusive formation of 1,3,3-trimethylbicyclo[2.2.1]hept-2-exo-yl acetate, implying an SN2 reaction mechanism.