2217-02-9

Basic information

• Product Name: (+)-Fenchol
• Synonyms: FENCHYL ALCOHOL;FEMA 2480;ALPHA FENCHOL;(1R)-1,3,3-TRIMETHYLBICYCLO[2.2.1]HEPTAN-2-OL;(1R)-ENDO-(+)-FENCHOL;(1R)-ENDO-(+)-FENCHYL ALCOHOL;1,3,3-TRIMETHYL-2-NORBORNANOL;(+)-Fenchol~1,3,3-Trimethyl-2-norbornanol
• CAS NO: 2217-02-9
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 216-639-5
• Product Categories: Miscellaneous
• Mol File: 2217-02-9.mol
• Article Data: 15

Chemical Properties

• Melting Point: 43-46 °C
• Boiling Point: 201-202 °C(lit.)
• Flash Point: 165 °F
• Appearance: /
• Density: 0.8389 (rough estimate)
• Vapor Pressure: 0.0693mmHg at 25°C
• Refractive Index: 1.4790 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 15.38±0.60(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 1850917
• CAS DataBase Reference: (+)-Fenchol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Fenchol(2217-02-9)
• EPA Substance Registry System: (+)-Fenchol(2217-02-9)

Safety Data

• Statements: 36/38
• Safety Statements: 22-24/25
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 2217-02-9(Hazardous Substances Data)

Usage

Chemical Properties

clear slightly yellow liquid after melting

Uses

Different sources of media describe the Uses of 2217-02-9 differently. You can refer to the following data:
1. Solvent, organic intermediate, odorant, flavoring.
2. (1R)-endo-(+)-Fenchyl alcohol?can be extensively used in daily chemicals such as fair antiperspirant, textile softener and liquid detergent. It can also be esterified by different kinds of organic acids to expand its usage in flavors and fragrances.

General Description

(1R)-endo-(+)-Fenchyl alcohol is a bicyclic monoterpenoid that contains a fenchane skeleton. It is a commonly used volatile compound in fragrances and flavoring agents.

InChI:InChI=1/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1

Synthetic route

(1R)-1,3,3-trimethyl-2-(2-methylprop-2-enyl)bicyclo[2.2.1]heptan-2-ol → (1R)-endo-(+)-fenchol (2217-02-9) + (1R,2R)-2-[(2S)-2-hydroxypropyl]-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol

Conditions	Yield
Stage #1: (1R)-1,3,3-trimethyl-2-(2-methylprop-2-enyl)bicyclo[2.2.1]heptan-2-ol With oxygen; ozone In diethyl ether at -78℃; Oxidation; Stage #2: With lithium aluminium tetrahydride In diethyl ether at -78 - 20℃; Reduction;	A 0.18 g B 79%

(1R)-fenchone (7787-20-4) → (1R)-endo-(+)-fenchol (2217-02-9)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether
With ethanol; sodium
With ammonia; lithium; ammonium chloride In tetrahydrofuran at -75℃; for 0.916667h; Yield given;

ethylmagnesium iodide (10467-10-4) + (1R)-fenchone (7787-20-4) → (1R)-endo-(+)-fenchol (2217-02-9) + (1R)-endo-2-ethylfenchol (137255-07-3)

Conditions	Yield
In diethyl ether for 8h; Heating;	A 84 % Chromat. B 13 % Chromat.

(1R)-fenchone (7787-20-4) → (1R)-endo-(+)-fenchylalcohol (64439-31-2) + (1R)-endo-(+)-fenchol (2217-02-9)

Conditions	Yield
With aluminum oxide; sodium; isopropyl alcohol In tetrahydrofuran for 5h; Heating;	A 44.0 % Chromat. B 56.0 % Chromat.
With aluminum isopropoxide; isopropyl alcohol for 420h; Heating;	A 1.02 g B n/a
With tropinone reductase of Cochlearia officinalis; NADPH In methanol at 30℃; for 1h; pH=5; Kinetics; Reagent/catalyst; Enzymatic reaction;

(+)-8-bromo-α-fenchol (146203-05-6) → (1R)-endo-(+)-fenchol (2217-02-9)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 6h; Ambient temperature;

1-[(1R,2R)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl]propan-2-one (251319-23-0) → (1R)-endo-(+)-fenchol (2217-02-9) + (1R,2R)-2-[(2S)-2-hydroxypropyl]-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol

Conditions	Yield
With lithium aluminium tetrahydride Reduction;

ethanol (64-17-5) + (1R)-fenchone (7787-20-4) + sodium → (1R)-endo-(+)-fenchylalcohol (64439-31-2) + (1R)-endo-(+)-fenchol (2217-02-9)

(1R)-2-ethenyl-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol → (1R)-endo-(+)-fenchol (2217-02-9) + (1R,2R)-2-(hydroxymethyl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol + (1R,2S)-2-(hydroxymethyl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol

Conditions	Yield
Stage #1: (1R)-2-ethenyl-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol With oxygen; ozone In diethyl ether at -78℃; Oxidation; Stage #2: With lithium aluminium tetrahydride In diethyl ether at -78 - 20℃; Reduction;	A 0.05 g B 0.07 g C n/a

(1R)-1,3,3-trimethyl-2-(2-methylprop-2-enyl)bicyclo[2.2.1]heptan-2-ol → (1R)-endo-(+)-fenchol (2217-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: O3/O2 / diethyl ether / -78 - 20 °C 2: LiAlH4 View Scheme
Multi-step reaction with 2 steps 1.1: O3/O2 / diethyl ether / -78 °C 1.2: 8.28 g / Et3N / diethyl ether / -78 - 20 °C 2.1: LiAlH4 View Scheme

(1R,4S)-2-Ethynyl-1,3,3-trimethyl-bicyclo[2.2.1]heptan-2-ol (18084-01-0, 21696-69-5, 131062-94-7, 137255-12-0, 137255-14-2) → (1R)-endo-(+)-fenchol (2217-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 59 percent Chromat. / N-methylpyrrolidone, potassium hydroxide / 4 h / 20 °C 2: 84 percent Chromat. / diethyl ether / 8 h / Heating View Scheme

(1R)-endo-(+)-fenchol (2217-02-9) → (1R)-fenchone (7787-20-4)

Conditions	Yield
With octahydro-2,5-epiminopentalen-7-yloxidanyl; acetic acid; sodium nitrite In acetonitrile at 20℃; for 5h; air;	100%
With Amberlyst A26 resin bound bis(azido)iodate(I) In acetonitrile at 20℃; for 6h; Irradiation; Inert atmosphere;	99%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 0.25h; Ambient temperature;	95%

(1R)-endo-(+)-fenchol (2217-02-9) → C20H34ClO3P

Conditions	Yield
Stage #1: (1R)-endo-(+)-fenchol With n-butyllithium In tetrahydrofuran; diethyl ether at -30℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: With trichlorophosphate In tetrahydrofuran; diethyl ether at -30 - 20℃; Inert atmosphere; Schlenk technique;	99%

methyl 3-pyridinecarboxylate (93-60-7) + (1R)-endo-(+)-fenchol (2217-02-9) → Nicotinic acid (1R,2R,4S)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane for 0.2h;	98%

(1R)-endo-(+)-fenchol (2217-02-9) + 1-cyano-2-methoxynaphthalene (16000-39-8) → 2-(((1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)oxy)-1-naphthonitrile

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 20℃; for 16h; Inert atmosphere; Sealed tube; Glovebox;	98%

(1R)-endo-(+)-fenchol (2217-02-9) → H-fenchyl phosphonate

Conditions	Yield
With hypophosphorous acid In toluene; acetonitrile at 85℃; for 24h;	97%

p-octyloxyphenyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside (916497-81-9) + (1R)-endo-(+)-fenchol (2217-02-9) → (+)-fenchyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Conditions	Yield
With trifluorormethanesulfonic acid; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane for 3h; Molecular sieve;	97%

pent-4-enoic acid (591-80-0) + (1R)-endo-(+)-fenchol (2217-02-9) → (2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl pent-4-enoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 36h;	96%

(1R)-endo-(+)-fenchol (2217-02-9) + benzyl 2-triethylsilyl-2-diazoacetate (443988-47-4) → Triethylsilanyl-((1R,2R,4S)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yloxy)-acetic acid benzyl ester

Conditions	Yield
dirhodium tetraacetate In toluene at 50℃; for 16h;	94%

(1R)-endo-(+)-fenchol (2217-02-9) + p-toluenesulfonyl chloride (98-59-9) → endo-fenchyl tosylate (350849-01-3)

Conditions	Yield
With pyridine at 60℃; for 168h; Inert atmosphere;	94%

(1R)-endo-(+)-fenchol (2217-02-9) + D-glucal triacetate (2873-29-2) → (1R)-endo-fenacholyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (1170710-39-0)

Conditions	Yield
With gadolinium(III) trifluoromethanesulfonate In acetonitrile at 20 - 40℃; Catalytic behavior; Ferrier Carbohydrate Rearrangement; diastereoselective reaction;	92%
With zinc dibromide In chloroform at 72℃; for 0.5h; Ferrier Carbohydrate Rearrangement; Microwave irradiation; stereoselective reaction;	88%
With (1S)-10-camphorsulfonic acid In dichloromethane at 20℃; for 3h; Ferrier rearrangement; stereoselective reaction;	84%
With triflic acid supported on silica gel at 40℃; for 0.166667h; Ferrier Carbohydrate Rearrangement;	72%

6-(((tert-butoxycarbonyl)amino)methyl)nicotinic acid (170097-87-7) + (1R)-endo-(+)-fenchol (2217-02-9) → α-fenchyl 6'-(tert-butoxycarbonylaminomethyl)nicotinate

Conditions	Yield
Stage #1: 6-(((tert-butoxycarbonyl)amino)methyl)nicotinic acid With 2,4,6-trichlorobenzoyl chloride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: (1R)-endo-(+)-fenchol With dmap In N,N-dimethyl-formamide; toluene at 20℃; for 16h;	90%

(1R)-endo-(+)-fenchol (2217-02-9) + 2-ethoxybenzoic acid (134-11-2) → C19H26O3

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 5h;	90%

(1R)-endo-(+)-fenchol (2217-02-9) + 2-Iodobenzoyl chloride (609-67-6) → (2R)-endo-fenchyl 2-iodobenzoate (1100747-72-5)

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 80℃;	88%

(1R)-endo-(+)-fenchol (2217-02-9) + sulfur trioxide pyridine complex (26412-87-3) → pyridinium (1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl sulfate

Conditions	Yield
With pyridine; acetic anhydride In toluene at 50℃;	88%

(1R)-endo-(+)-fenchol (2217-02-9) + 4-(1,1-dimethylethyl)benzoic acid (98-73-7) → C21H30O2

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h;	88%

(1R)-endo-(+)-fenchol (2217-02-9) + acetic anhydride (108-24-7) → endo-bicyclo[2,2,1]heptan-2-ol-1,3,3-trimethyl acetate (99341-77-2)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 72h; Inert atmosphere;	85%
With pyridine
With sodium acetate

formaldehyd (50-00-0) + (1R)-endo-(+)-fenchol (2217-02-9) → bis(((1R,2R,4S)‑1,3,3‑trimethylbicyclo[2.2.1]heptan‑2‑yl)oxy)methane

Conditions	Yield
With toluene-4-sulfonic acid In toluene Dean-Stark; Reflux;	85%
In toluene

(1R)-endo-(+)-fenchol (2217-02-9) + Trifluoro-methanesulfonate4-benzyl-1-(2,2-dimethyl-propionyl)-pyridinium; → 2,2-Dimethyl-propionic acid (1R,2R,4S)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Conditions	Yield
In dichloromethane for 16h; Ambient temperature;	82%

fumaryl dichloride (627-63-4) + (1R)-endo-(+)-fenchol (2217-02-9) → di(+)-fenchyl fumarate (593279-35-7)

Conditions	Yield
In toluene for 20h; Heating;	79%

(1R)-endo-(+)-fenchol (2217-02-9) + Trifluoro-methanesulfonate1-benzoyl-4-benzyl-pyridinium; → Benzoic acid (1R,2R,4S)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Conditions	Yield
In dichloromethane for 16h; Ambient temperature;	78%

(1R)-endo-(+)-fenchol (2217-02-9) + 2,3,4,-trifluorobenzoic acid (61079-72-9) → C17H19F3O2

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12h;	78%

(1R)-endo-(+)-fenchol (2217-02-9) + naphthalene-2-carboxylate (93-09-4) → C21H24O2

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 8h;	78%

(1R)-endo-(+)-fenchol (2217-02-9) + 4-trifluoromethylbenzoic acid (455-24-3) → C18H21F3O2

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 10h;	77%

(1R)-endo-(+)-fenchol (2217-02-9) + benzyl alcohol (100-51-6) → C17H24O

Conditions	Yield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold (I) at 150℃; for 0.5h; Inert atmosphere; Microwave irradiation;	76%

(1R)-endo-(+)-fenchol (2217-02-9) + (E)-1,2-bis(phenylsulfonyl)ethylene (963-16-6) → (E)-1-(2-fenchyloxy)-2-phenylsulfonyl ethylene

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -78℃;	75%

(1R)-endo-(+)-fenchol (2217-02-9) + N-benzyloxycarbonyl-D-alanine (26607-51-2) → N-benzyloxycarbonyl-D-alanine (+)-α-fenchyl ester (108646-35-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6.5h;	72.5%

C33H35Cl4NO7 (1133063-10-1) + (1R)-endo-(+)-fenchol (2217-02-9) → C41H51ClO7 (1133062-98-2)

Conditions	Yield
With 2-chloro-6-methylpyridinium triflate In hexane for 0.5h; Inert atmosphere;	72%

(1R)-endo-(+)-fenchol (2217-02-9) + chloroacetyl chloride (79-04-9) → (1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl 2-chloroacetate

Conditions	Yield
With triethylamine In dichloromethane at 15 - 25℃; for 12h; Inert atmosphere;	72%

(1R)-endo-(+)-fenchol (2217-02-9) + acryloyl chloride (814-68-6) → (1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl acrylate (219580-52-6)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h;	70%

Upstream product

• 7787-20-4 (1R)-fenchone 
• 67-63-0 isopropyl alcohol 
• 4695-62-9 (+)-fenchone 
• 7787-20-4 (-)-1,3,3-trimethyl-2-norbornanone 
• 18492-37-0 (+/-)-fenchone 
• 555-31-7 aluminum isopropoxide 
• 4695-62-9 fenchone 
• 75-05-8 acetonitrile 
• 107-13-1 acrylonitrile 
• 109-74-0 propyl cyanide 
• 18084-01-0 (1R,4S)-2-Ethynyl-1,3,3-trimethyl-bicyclo[2.2.1]heptan-2-ol 
• 64-17-5 ethanol 
• 251319-23-0 1-[(1R,2R)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl]propan-2-one 
• 146203-05-6 (+)-8-bromo-α-fenchol 

Downstream Products

• 4695-62-9 fenchone 
• 350849-01-3 endo-fenchyl tosylate 
• 1240724-47-3 C₂₃H₃₂O₄ 
• 1240724-49-5 C₃₁H₄₈O₄ 
• 13851-11-1 α-fenchyl acetate 
• 7787-20-4 (1R)-fenchone 
• 1357075-81-0 2-fenchyl (R)-2-methoxy-2-phenylpent-3-ynoate 
• 1357075-82-1 2-fenchyl (S)-2-methoxy-2-phenylpent-3-ynoate 
• 1133062-98-2 C₄₁H₅₁ClO₇ 
• 103300-55-6 N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-D-phenylglycine (-)-α-fenchyl ester 
• 103300-55-6 (S)-3-Benzyloxycarbonylamino-N-[phenyl-((1S,2R,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yloxycarbonyl)-methyl]-succinamic acid benzyl ester 
• 103366-56-9 L-aspartyl-D-phenylglycine (-)-α-fenchyl ester 
• 103300-60-3 (S)-3-Amino-N-[phenyl-((1S,2R,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yloxycarbonyl)-methyl]-succinamic acid 

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