7540-51-4

Basic information

• Product Name: BETA-RHODINOL
• Synonyms: (S)-(-)-3,7-DIMETHYL-6-OCTEN-1-OL;(S)-3,7-DIMETHYL-6-OCTEN-1-OL;(S)-(-)-BETA-CITRONELLOL;(S)-(-)-3,7-dimethyl-oct-6-en-1-ol;3,7-dimethyl-,(S)-6-Octen-1-ol;7-dimethyl-(s)-6-octen-1-o;BETA-RHODINOL;(-)-BETA-CITRONELLAL
• CAS NO: 7540-51-4
• Molecular Formula: C₁₀H₂₀O
• Molecular Weight: 156.27
• EINECS: 231-415-7
• Product Categories: All Aliphatics;Acyclic Monoterpenes;Biochemistry;Terpenes;Aliphatics;Chiral Reagents
• Mol File: 7540-51-4.mol
• Article Data: 57

Chemical Properties

• Boiling Point: 225-226 °C(lit.)
• Flash Point: 210 °F
• Appearance: Clear colorless liquid
• Density: 0.856 g/mL at 25 °C(lit.)
• Vapor Pressure: ~0.02 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.456
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Soluble), Ethyl Acetate (Slightly), Methanol (Soluble)
• PKA: 15.13±0.10(Predicted)
• Water Solubility: SLIGHTLY SOLUBLE
• Merck: 14,2330
• BRN: 1721505
• CAS DataBase Reference: BETA-RHODINOL(CAS DataBase Reference)
• NIST Chemistry Reference: BETA-RHODINOL(7540-51-4)
• EPA Substance Registry System: BETA-RHODINOL(7540-51-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: RH3404000
• F: 8-10
• TSCA: Yes
• Hazardous Substances Data: 7540-51-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear Colorless Liquid

Uses

L-Citronellol as fragrance ingredient.

Definition

ChEBI: A citronellol that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7 (the 3S-enantiomer).

General Description

Citronellol is a monoterpene alcohol found in essential oils of Cymbopogon winterianus Jowitt. S-(?)-isomer that is less common. It is prevalent in geranium and citronella oils.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m1/s1

Synthetic route

Geraniol (106-24-1) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; (RC,SFc,SP)-1-[2-(1-N,N-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1'-dicyclohexylphosphinoferrocene; hydrogen In dichloromethane at 20℃; under 19001.3 Torr; for 20h; Inert atmosphere; Autoclave; enantioselective reaction;	99%
With [RuCl(p-cymene)((R)-Tol-BINAP)]Cl; potassium hydroxide In isopropyl alcohol for 2h; Inert atmosphere; Reflux;	70%
Multi-step reaction with 2 steps 1: in Ficus retusa Linn. 2: in Ficus retusa Linn. nach Injektion View Scheme

3,7-dimethyl-2,6-octadienal (141-27-5) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With dichloro(1,5-cyclooctadiene)ruthenium(II); (R)-(+)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; niobium pentachloride; HSiPh3 In toluene at 40℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Glovebox; Sealed tube; Inert atmosphere; enantioselective reaction;	98.59%
With (η4-cyclooctadiene)((R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl)rhodium(I) tetrfluoroborate; hydrogen In methanol at 60℃; under 33753.4 Torr; for 5h; Autoclave; enantioselective reaction;	88%

Carbonic acid (S)-3,7-dimethyl-oct-6-enyl ester 2,2,2-trichloro-ethyl ester → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With indium; water; ammonium chloride In methanol for 1h; Heating;	98%

(S)-Citronellal (5949-05-3) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether	96%
With lithium aluminium tetrahydride In diethyl ether	94%
With sodium tetrahydroborate In ethanol at 0℃;	93%

Trichloro-acetic acid (S)-3,7-dimethyl-oct-6-enyl ester → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With indium; water; ammonium chloride In methanol for 0.5h; Heating;	95%

(R)-2-(3,7-dimethyloct-6-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With sodium perborate; water In tetrahydrofuran at 20℃; for 4h; enantioselective reaction;	95%

2,2-dimethyl-propionic acid (3S)-3,7-dimethyl-oct-6-enyl ester (93041-00-0) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With sodium hydroxide In methanol Ambient temperature;	94%

(S)-8-(allyloxy)-2,6-dimethyloct-2-ene → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
Stage #1: (S)-8-(allyloxy)-2,6-dimethyloct-2-ene With C12H37NiP4(1+)*C2F6NO4S2(1-) In tetrahydrofuran at 20℃; for 0.5h; Glovebox; Schlenk technique; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran for 1.5h; Glovebox; Schlenk technique; Reflux; Inert atmosphere;	94%

(S)-3,7-Dimethyl-oct-6-enoic acid (1S,2R,3S,4R)-3-(2,2-dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (89156-40-1) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (1R,2S,3R,4S)-2-(2,2-dimethylpropoxy)-1,7,7-trimethylbicyclo<2.2.1>heptan-3-ol (85695-96-1)

Conditions	Yield
With lithium aluminium tetrahydride	A 88% B 81%

(S)-((3,7-dimethyloct-6-enyloxy)methyl)benzene (84237-05-8) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With ammonia; lithium In tetrahydrofuran at -30℃; for 0.666667h;	82%

(S)-8-(2,3-dimethyl-but-2-en-1-yloxy)-2,6-dimethyloct-2-ene → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With (PhSO2)2; water In dichloromethane at 80℃;	82%

(S)-Citronellal (5949-05-3) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (S)-(-)-citronellic acid (2111-53-7)

Conditions	Yield
With Fusarium concentricum In dimethyl sulfoxide at 28 - 30℃; for 120h; Reagent/catalyst; Microbiological reaction;	A 76% B 5%
With Fusarium fujikuroi In dimethyl sulfoxide at 28 - 30℃; for 120h; Microbiological reaction;	A 36% B 43%
With endosperms of Triticum aestivum L. cv Dariel wheat seeds In water at 27℃; Reagent/catalyst; Concentration; Darkness; Enzymatic reaction; enantioselective reaction;

Nerol (106-25-2) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; potassium hydroxide at 100℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	70%
With hydrogen; BINAP-Ru(II) dicarboxylate In methanol at 18 - 20℃; Yield given;
With hydrogen; BINAP-(Ru(II) dicarboxylate In methanol at 18 - 20℃; Product distribution; examination of enantioselectivity; various complexes;

(S)-(-)-citronellic acid (2111-53-7) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 3h; Inert atmosphere;	69%

(S)-Citronellal (5949-05-3) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (1S,3R,4S)-p-menthane-3,8-diol (19956-48-0) + (1S,3S,4S)-p-menthane-3,8-diol (3564-95-2, 3564-98-5, 19956-48-0, 42822-86-6, 81176-87-6, 81176-88-7, 91739-72-9, 91739-73-0, 92471-23-3, 107133-84-6, 138663-70-4, 140924-71-6) + (−)-neo-isopulegol (122517-60-6) + (+)-isopulegol

Conditions	Yield
With Penicillium paxilli In dimethyl sulfoxide at 28 - 30℃; for 120h; Microbiological reaction;	A 10% B 50% C 20% D 5% E 2%

(S)-citronellyl propionate → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With potassium chloride; water In acetone	48%

3,7-dimethyl-oct-6-enal (106-23-0, 26489-02-1) → (R)-Citronellal (2385-77-5) + (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With baker's yeast	A 21% B 33%

(S)-(-)-3,7-dimethyl-6-ocyten-1-yl diphenylmethylsilyl ether → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With potassium (4-methylphenyl)trifluoroborate In dimethyl sulfoxide at 37℃; for 24h; Inert atmosphere;	18%

ethanol (64-17-5) + (S)-Citronellal (5949-05-3) + EtOMgCl → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

(E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
in Ficus retusa Linn. nach Injektion;

Nerol (106-25-2) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9)

Conditions	Yield
With hydrogen; <(+)-CyBINAP>-RhN In benzene under 15200 Torr; Ambient temperature; Yield given. Yields of byproduct given;
With hydrogen; ClO4 In benzene under 7600 Torr; for 8h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3 In methanol at 19.9℃; under 1807.6 Torr; Product distribution; different pressure and temperature;
With 1,2-bis(2,5-diisopropylphospholano)benzene; potassium hydroxide at 100℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

Geraniol (106-24-1) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9) + (R)-3,7-dimethyloctan-1-ol (1117-60-8)

Conditions	Yield
With hydrogen; {RuI((R)-2,2'-bis(diphenylphospino)-1,1'-binaphthyl)(p-cymene)}I In methanol; water at 20℃; under 76000 Torr; for 8h; Yield given. Yields of byproduct given;

Geraniol (106-24-1) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9)

Conditions	Yield
With <<(-)-2,2'-bis(diphenylphosphino)-4,4',6,6'-tetramethyl-3,3'-bibenzothiophene>Ru(p-cumene)I>I; hydrogen In methanol at 25℃; under 7355.08 Torr; for 88h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With ((S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine))Ru(O2CCF3)2; hydrogen In methanol at 20 - 25℃; under 45003.6 Torr; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; <(+)-BINAP>RhN In benzene under 22800 Torr; Ambient temperature; Yield given. Yields of byproduct given;

(R)-1-[(R)-3-(1-Hydroxy-1-methyl-ethyl)-pyrrolidin-1-yl]-3,7-dimethyl-oct-6-en-1-one → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9)

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran Ambient temperature; Yield given;
With lithium triethylborohydride In tetrahydrofuran Ambient temperature; Yields of byproduct given;

N,N-diethyl-N-{1-[(3S),7-dimethylocta-1,6-dienyl]}amine (67392-54-5) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With oxonium; hydrogen

(S)-(+)-dihydromyrcene (2436-90-0) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate; 2-methyl-but-2-ene; boron trifluoride; dihydrogen peroxide 1.) THF, room temp., 3 h.; 2.) 50 deg C, 1.5 h; Multistep reaction;

γ-geraniol (13066-51-8) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9)

Conditions	Yield
With Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3; hydrogen In methanol at 19.9℃; under 3750.3 Torr; Title compound not separated from byproducts;
With hydrogen; Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3 In methanol at 19.9℃; under 1807.6 Torr; Product distribution; other pressure and temperature;
With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; potassium hydroxide at 100℃; for 6h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

(3S)-3,7-dimethyl-6-octen-1-yl acetate (67601-05-2) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
Stage #1: (3S)-3,7-dimethyl-6-octen-1-yl acetate With sodium hydroxide In ethanol at 90℃; for 3h; Alkaline hydrolysis; Stage #2: With Pichia kluyveri IFO 1165 at 30℃; for 48h;

vinyl acetate (108-05-4) + Citronellol (106-22-9) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9) + (R)-1-citronellyl acetate (20425-54-1) + (3S)-3,7-dimethyl-6-octen-1-yl acetate (67601-05-2)

Conditions	Yield
With porcine pancreatic lipase In hexane for 24h; Title compound not separated from byproducts;
With porcine pancreatic lipase In hexane for 48h; Title compound not separated from byproducts;

Geraniol (106-24-1) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; (RC,SFc,SP)-1-[2-(1-N,N-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1'-dicyclohexylphosphinoferrocene; hydrogen In dichloromethane at 20℃; under 19001.3 Torr; for 20h; Inert atmosphere; Autoclave; enantioselective reaction;	99%
With [RuCl(p-cymene)((R)-Tol-BINAP)]Cl; potassium hydroxide In isopropyl alcohol for 2h; Inert atmosphere; Reflux;	70%
Multi-step reaction with 2 steps 1: in Ficus retusa Linn. 2: in Ficus retusa Linn. nach Injektion View Scheme

3,7-dimethyl-2,6-octadienal (141-27-5) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With dichloro(1,5-cyclooctadiene)ruthenium(II); (R)-(+)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; niobium pentachloride; HSiPh3 In toluene at 40℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Glovebox; Sealed tube; Inert atmosphere; enantioselective reaction;	98.59%
With (η4-cyclooctadiene)((R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl)rhodium(I) tetrfluoroborate; hydrogen In methanol at 60℃; under 33753.4 Torr; for 5h; Autoclave; enantioselective reaction;	88%

Carbonic acid (S)-3,7-dimethyl-oct-6-enyl ester 2,2,2-trichloro-ethyl ester → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With indium; water; ammonium chloride In methanol for 1h; Heating;	98%

(S)-Citronellal (5949-05-3) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether	96%
With lithium aluminium tetrahydride In diethyl ether	94%
With sodium tetrahydroborate In ethanol at 0℃;	93%

Trichloro-acetic acid (S)-3,7-dimethyl-oct-6-enyl ester → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With indium; water; ammonium chloride In methanol for 0.5h; Heating;	95%

(R)-2-(3,7-dimethyloct-6-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With sodium perborate; water In tetrahydrofuran at 20℃; for 4h; enantioselective reaction;	95%

2,2-dimethyl-propionic acid (3S)-3,7-dimethyl-oct-6-enyl ester (93041-00-0) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With sodium hydroxide In methanol Ambient temperature;	94%

(S)-8-(allyloxy)-2,6-dimethyloct-2-ene → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
Stage #1: (S)-8-(allyloxy)-2,6-dimethyloct-2-ene With C12H37NiP4(1+)*C2F6NO4S2(1-) In tetrahydrofuran at 20℃; for 0.5h; Glovebox; Schlenk technique; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran for 1.5h; Glovebox; Schlenk technique; Reflux; Inert atmosphere;	94%

(S)-3,7-Dimethyl-oct-6-enoic acid (1S,2R,3S,4R)-3-(2,2-dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (89156-40-1) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (1R,2S,3R,4S)-2-(2,2-dimethylpropoxy)-1,7,7-trimethylbicyclo<2.2.1>heptan-3-ol (85695-96-1)

Conditions	Yield
With lithium aluminium tetrahydride	A 88% B 81%

(S)-((3,7-dimethyloct-6-enyloxy)methyl)benzene (84237-05-8) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With ammonia; lithium In tetrahydrofuran at -30℃; for 0.666667h;	82%

(S)-8-(2,3-dimethyl-but-2-en-1-yloxy)-2,6-dimethyloct-2-ene → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With (PhSO2)2; water In dichloromethane at 80℃;	82%

(S)-Citronellal (5949-05-3) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (S)-(-)-citronellic acid (2111-53-7)

Conditions	Yield
With Fusarium concentricum In dimethyl sulfoxide at 28 - 30℃; for 120h; Reagent/catalyst; Microbiological reaction;	A 76% B 5%
With Fusarium fujikuroi In dimethyl sulfoxide at 28 - 30℃; for 120h; Microbiological reaction;	A 36% B 43%
With endosperms of Triticum aestivum L. cv Dariel wheat seeds In water at 27℃; Reagent/catalyst; Concentration; Darkness; Enzymatic reaction; enantioselective reaction;

Nerol (106-25-2) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; potassium hydroxide at 100℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	70%
With hydrogen; BINAP-Ru(II) dicarboxylate In methanol at 18 - 20℃; Yield given;
With hydrogen; BINAP-(Ru(II) dicarboxylate In methanol at 18 - 20℃; Product distribution; examination of enantioselectivity; various complexes;

(S)-(-)-citronellic acid (2111-53-7) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 3h; Inert atmosphere;	69%

(S)-Citronellal (5949-05-3) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (1S,3R,4S)-p-menthane-3,8-diol (19956-48-0) + (1S,3S,4S)-p-menthane-3,8-diol (3564-95-2, 3564-98-5, 19956-48-0, 42822-86-6, 81176-87-6, 81176-88-7, 91739-72-9, 91739-73-0, 92471-23-3, 107133-84-6, 138663-70-4, 140924-71-6) + (−)-neo-isopulegol (122517-60-6) + (+)-isopulegol (104870-56-6)

Conditions	Yield
With Penicillium paxilli In dimethyl sulfoxide at 28 - 30℃; for 120h; Microbiological reaction;	A 10% B 50% C 20% D 5% E 2%

(S)-citronellyl propionate → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With potassium chloride; water In acetone	48%

3,7-dimethyl-oct-6-enal (106-23-0, 26489-02-1) → (R)-Citronellal (2385-77-5) + (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With baker's yeast	A 21% B 33%

(S)-(-)-3,7-dimethyl-6-ocyten-1-yl diphenylmethylsilyl ether → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With potassium (4-methylphenyl)trifluoroborate In dimethyl sulfoxide at 37℃; for 24h; Inert atmosphere;	18%

ethanol (64-17-5) + (S)-Citronellal (5949-05-3) + EtOMgCl → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

(E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
in Ficus retusa Linn. nach Injektion;

Nerol (106-25-2) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9)

Conditions	Yield
With hydrogen; <(+)-CyBINAP>-RhN In benzene under 15200 Torr; Ambient temperature; Yield given. Yields of byproduct given;
With hydrogen; ClO4 In benzene under 7600 Torr; for 8h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3 In methanol at 19.9℃; under 1807.6 Torr; Product distribution; different pressure and temperature;
With 1,2-bis(2,5-diisopropylphospholano)benzene; potassium hydroxide at 100℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

Geraniol (106-24-1) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9) + (R)-3,7-dimethyloctan-1-ol (1117-60-8)

Conditions	Yield
With hydrogen; {RuI((R)-2,2'-bis(diphenylphospino)-1,1'-binaphthyl)(p-cymene)}I In methanol; water at 20℃; under 76000 Torr; for 8h; Yield given. Yields of byproduct given;

Geraniol (106-24-1) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9)

Conditions	Yield
With <<(-)-2,2'-bis(diphenylphosphino)-4,4',6,6'-tetramethyl-3,3'-bibenzothiophene>Ru(p-cumene)I>I; hydrogen In methanol at 25℃; under 7355.08 Torr; for 88h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With ((S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine))Ru(O2CCF3)2; hydrogen In methanol at 20 - 25℃; under 45003.6 Torr; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; <(+)-BINAP>RhN In benzene under 22800 Torr; Ambient temperature; Yield given. Yields of byproduct given;

(R)-1-[(R)-3-(1-Hydroxy-1-methyl-ethyl)-pyrrolidin-1-yl]-3,7-dimethyl-oct-6-en-1-one → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9)

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran Ambient temperature; Yield given;
With lithium triethylborohydride In tetrahydrofuran Ambient temperature; Yields of byproduct given;

N,N-diethyl-N-{1-[(3S),7-dimethylocta-1,6-dienyl]}amine (67392-54-5) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With oxonium; hydrogen

(S)-(+)-dihydromyrcene (2436-90-0) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate; 2-methyl-but-2-ene; boron trifluoride; dihydrogen peroxide 1.) THF, room temp., 3 h.; 2.) 50 deg C, 1.5 h; Multistep reaction;

γ-geraniol (13066-51-8) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9)

Conditions	Yield
With Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3; hydrogen In methanol at 19.9℃; under 3750.3 Torr; Title compound not separated from byproducts;
With hydrogen; Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3 In methanol at 19.9℃; under 1807.6 Torr; Product distribution; other pressure and temperature;
With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; potassium hydroxide at 100℃; for 6h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

(3S)-3,7-dimethyl-6-octen-1-yl acetate (67601-05-2) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Conditions	Yield
Stage #1: (3S)-3,7-dimethyl-6-octen-1-yl acetate With sodium hydroxide In ethanol at 90℃; for 3h; Alkaline hydrolysis; Stage #2: With Pichia kluyveri IFO 1165 at 30℃; for 48h;

vinyl acetate (108-05-4) + Citronellol (106-22-9) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (3R)-citronellol (1117-61-9) + (R)-1-citronellyl acetate (20425-54-1) + (3S)-3,7-dimethyl-6-octen-1-yl acetate (67601-05-2)

Conditions	Yield
With porcine pancreatic lipase In hexane for 24h; Title compound not separated from byproducts;
With porcine pancreatic lipase In hexane for 48h; Title compound not separated from byproducts;

(S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) → S-(-)-dihydrocitronellol (68680-98-8)

Conditions	Yield
With palladium on activated charcoal; hydrogen	100%
With palladium on activated charcoal; hydrogen In methanol; ethyl acetate at 25℃; for 18h; Inert atmosphere;	98%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 0.25h; Inert atmosphere;	96%

(S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + p-toluenesulfonyl chloride (98-59-9) → (S)-3,7-dimethyl-6-octenyl tosylate (41144-01-8, 67214-54-4, 93303-23-2, 116661-43-9)

Conditions	Yield
With pyridine at 0℃; for 12h; Tosylation;	100%
With pyridine at 0℃; for 72h;	100%
With pyridine	100%

Upstream product

• 64-17-5 ethanol 
• 5949-05-3 (S)-Citronellal 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 84237-05-8 (S)-((3,7-dimethyloct-6-enyloxy)methyl)benzene 
• 13066-51-8 γ-geraniol 
• 108-05-4 vinyl acetate 
• 106-22-9 Citronellol 
• 106-26-3 cis-3,7-dimethyl-2,6-octadienal 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 2111-53-7 (S)-(-)-citronellic acid 
• 106-24-1 Geraniol 
• 64504-53-6 2-methylpent-2-en-5-yl lithium 
• 93041-04-4 (3R)-7-methyl3-(tosyloxy)oct-6-enyl pivalate 

Downstream Products

• 5949-05-3 (S)-Citronellal 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 137225-55-9 5-(4-Decyloxy-phenyl)-2-((S)-3,7-dimethyl-oct-6-enyloxy)-pyrimidine 
• 52745-93-4 (4R)-4-methylhexanoic acid 
• 2385-77-5 (R)-Citronellal 
• 10340-84-8 (S)-citronellyl bromide 
• 67214-54-4 (R)-citronellyl tosylate 
• 41144-01-8 (S)-3,7-dimethyl-6-octenyl tosylate 
• 67601-05-2 (3S)-3,7-dimethyl-6-octen-1-yl acetate 
• 67245-12-9 (3R)-1-(benzyloxy)-3,7-dimethyl-6-octene 
• 64309-03-1 (3S,6RS)-3-Methyl-6-isopropenyl-9-decen-1-yl Acetate 
• 84237-05-8 (S)-((3,7-dimethyloct-6-enyloxy)methyl)benzene 
• 281661-30-1 (S)-tert-butyl (3,7-dimethyloct-6-enyloxy)diphenylsilane 
• 221632-62-8 (6S)-2,6-dimethyl-8-phenylthiooct-2-ene 

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