6169-06-8

Basic information

• Product Name: D(+)-2-Octanol
• Synonyms: D(+)-2-OCTANOL;D-2-OCTANOL;(s)-2-octano;(S)-octan-2-ol;(S)-(+)-2-HYDROXYOCTANE;(S)-2-HYDROXYOCTANE;(S)-(+)-2-OCTANOL;(S)-2-OCTANOL
• CAS NO: 6169-06-8
• Molecular Formula: C₈H₁₈O
• Molecular Weight: 130.23
• EINECS: 228-213-6
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds;chiral;Building Blocks for Liquid Crystals;Chiral Building Blocks;Chiral Compounds (Building Blocks for Liquid Crystals);Functional Materials;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Compound;AlcoholsDerivatization Reagents;Chiral GC Derivatization Reagents;Chiral Building Blocks;Chiral Derivatization;ChiralDerivatization Reagents;Derivatization Reagents HPLC;Organic Building Blocks
• Mol File: 6169-06-8.mol
• Article Data: 192

Chemical Properties

• Melting Point: -61.15°C (estimate)
• Boiling Point: 175 °C(lit.)
• Flash Point: 160 °F
• Appearance: Colorless to light yellow liquid
• Density: 0.822 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.426(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 1.28g/l
• PKA: 15.44±0.20(Predicted)
• Explosive Limit: 0.8%(V)
• Water Solubility: 1 g/L (20 ºC)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents
• Merck: 14,6752
• BRN: 1719323
• CAS DataBase Reference: D(+)-2-Octanol(CAS DataBase Reference)
• NIST Chemistry Reference: D(+)-2-Octanol(6169-06-8)
• EPA Substance Registry System: D(+)-2-Octanol(6169-06-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 6169-06-8(Hazardous Substances Data)

Usage

Description

D(+)-2-Octanol, also known as 2-Octanol, is a fatty alcohol that is directly produced from vegetal chemistry. It is obtained through a cracking process from castor oil and is primarily used as a raw material for the production of various compounds and as a green solvent in different industries.

Uses

Used in Flavor Industry:
D(+)-2-Octanol is used as a raw material to produce caproic acid, an intermediate in flavor production.
Used in Paints and Coatings Industry:
D(+)-2-Octanol is used as a green solvent for various resins intended for paints and coatings or adhesives sectors.
Used in Manufacturing Processes:
D(+)-2-Octanol can be employed as a defoamer in different processes, as an additive for lubricants, and as a solvent in rare minerals extraction.
Used in Coal Industry:
In the coal industry, D(+)-2-Octanol is used as a floatation agent and as a frother in mineral flotation.
Used in Synthesis of Compounds:
As an intermediate, D(+)-2-Octanol can be used in the synthesis of a wide range of plasticizers, esters, and surfactants, which include alcohol alkoxylates and sulfates for detergency and personal care markets; adipates, aebacates, palmitates, stearates for applications in cosmetic, paints and coatings, plastic, paper, textile, etc.; phthalates; acrylates and maleates for coatings and adhesives markets; salicylate, myristate, méthoxycinnamate for application in fragrances.
Used in Chiral Compounds:
D(+)-2-Octanol is used as chiral compounds.
Used in Research and Development:
D(+)-2-Octanol can be used to prepare the solution of 5-(benzyloxy)-isophthalic acid derivative, which is used as a 2D chiral self-assembly system comprising pyrolytic graphite. It also serves as a chiral template in the study of enantioselective glycidol esterification and as a starting material for the preparation of (+)-(S)-2-octyI tosylate, an intermediate used to prepare (?)-(R)-2-halo and azido octanes.

References

[1] https://en.wikipedia.org/wiki/2-Octanol [2] Robert A. Levis (2016) Hawley's Condensed Chemical Dictionary [3] http://www.castoroil.in/castor/castor_seed/castor_oil/2_octanol/2_octanol.html

InChI:InChI=1/C8H18O/c1-3-4-5-6-7-8(2)9/h8-9H,3-7H2,1-2H3

Synthetic route

(R)-2-octyl sulfate (74403-68-2) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With His-tagged Pseudomonas sp. metallo-β-lactamase-type alkylsulfatase Pisa1; water; tris hydrochloride at 30℃; for 6h; pH=8.2; Enzymatic reaction; optical yield given as %ee; stereoselective reaction;	100%

rac-octan-2-ol (4128-31-8) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With alcohol dehydrogenase from Lactobacillus kefir; alcohol dehydrogenase from Rhodococcus ruber DSM 44541; YcnD-oxidoreductase at 30℃; for 3h; pH=7.5; aq. buffer; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantiospecific reaction;	99%
With phosphate buffer; tributyrin for 140h; Ambient temperature;	77%

hexyl-methyl-ketone (111-13-7) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With NAD; Co2+immobilized acetophenone reductase from Geotrichum candidum In aq. phosphate buffer; isopropyl alcohol at 30℃; for 3h; pH=7.2; Green chemistry; Enzymatic reaction; enantioselective reaction;	99%
With glucose dehydrogenase; D-Glucose; alcohol dehydrogenase from Thermoanaerobacter sp.; NADPH In aq. buffer at 30℃; for 24h; pH=7.5; Concentration; Time; Ionic liquid; Green chemistry; Enzymatic reaction; enantioselective reaction;	85%
With acetophenone reductase from Geotrichum candidum NBRC 4597; NAD In isopropyl alcohol at 30℃; for 3h; pH=7.2; Enzymatic reaction; enantioselective reaction;	85%

(R)-2-octyl sulfate (74403-68-2) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With His-tagged Pseudomonas sp. metallo-β-lactamase-type alkylsulfatase Pisa1; water; tris hydrochloride at 30℃; for 6h; pH=8.2; Enzymatic reaction; optical yield given as %ee; stereoselective reaction;	100%

rac-octan-2-ol (4128-31-8) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With alcohol dehydrogenase from Lactobacillus kefir; alcohol dehydrogenase from Rhodococcus ruber DSM 44541; YcnD-oxidoreductase at 30℃; for 3h; pH=7.5; aq. buffer; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantiospecific reaction;	99%
With phosphate buffer; tributyrin for 140h; Ambient temperature;	77%

hexyl-methyl-ketone (111-13-7) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With NAD; Co2+immobilized acetophenone reductase from Geotrichum candidum In aq. phosphate buffer; isopropyl alcohol at 30℃; for 3h; pH=7.2; Green chemistry; Enzymatic reaction; enantioselective reaction;	99%
With glucose dehydrogenase; D-Glucose; alcohol dehydrogenase from Thermoanaerobacter sp.; NADPH In aq. buffer at 30℃; for 24h; pH=7.5; Concentration; Time; Ionic liquid; Green chemistry; Enzymatic reaction; enantioselective reaction;	85%
With acetophenone reductase from Geotrichum candidum NBRC 4597; NAD In isopropyl alcohol at 30℃; for 3h; pH=7.2; Enzymatic reaction; enantioselective reaction;	85%

rac-octan-2-ol (4128-31-8) → (S)-2-Octanol (6169-06-8) + (R)-Octan-2-ol (5978-70-1) + hexyl-methyl-ketone (111-13-7)

Conditions	Yield
With Arthrobacter atrocyaneus In N,N-dimethyl-formamide at 32℃; for 48h; Microbiological reaction; enantioselective reaction;	A 94% B n/a C n/a
With lyophilised cells of Escherichia coli overexpressing the solvent-tolerant alcohol dehydrogenase from Rhodococcus ruber DSM44541 In aq. buffer at 30℃; for 24h; pH=7.5; Reagent/catalyst; Resolution of racemate; Enzymatic reaction;	A n/a B n/a C n/a
With NADP In acetone at 50℃; for 22h; pH=8; Resolution of racemate;

(R)-(+)-2-hydroxyoctyl tosylate (111221-79-5) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran	93%

2-{[(S)-octan-7-yloxy]carbonyl}benzoic acid (6114-64-3) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With water; sodium hydroxide In methanol for 6h; Reflux; Inert atmosphere;	87%
With potassium hydroxide Heating;	3.4 g

rac-2-octyl sulfate (34760-88-8) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
Stage #1: rac-2-octyl sulfate With His-tagged Pseudomonas sp. metallo-β-lactamase-type alkylsulfatase Pisa1; water; tris hydrochloride at 30℃; for 24h; pH=8.2; Resolution of racemate; Enzymatic reaction; Stage #2: With water; toluene-4-sulfonic acid In 1,4-dioxane; tert-butyl methyl ether at 40℃; for 5h; optical yield given as %ee; stereoselective reaction;	87%
Multi-step reaction with 2 steps 1: His-tagged Pseudomonas sp. metallo-β-lactamase-type alkylsulfatase Pisa1; water; tris hydrochloride / 6 h / 30 °C / pH 8.2 / Resolution of racemate; Enzymatic reaction 2: water; toluene-4-sulfonic acid / 1,4-dioxane; tert-butyl methyl ether / 2 h / 40 °C View Scheme

(R)-1-Benzylsulfanyl-octan-2-ol → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With sodium hypophosphite; Raney-Ni (W-2) In ethanol; water for 0.5h; Ambient temperature; pH=5.2;	85%
With sodium hypophosphite; Raney Ni(W-2) In ethanol; water for 0.5h; Ambient temperature;	75%

(S)-N-(oct-2-yloxy)-4-(p-chlorophenyl)-thiazole-2(3H)-thione (1200233-22-2) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With tri-n-butyl-tin hydride In dichloromethane at 18℃; for 0.416667h; Inert atmosphere; Photolysis; enantioselective reaction;	85%

(R)-1-Phenylsulfanyl-octan-2-ol (140421-08-5) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With sodium hypophosphite; Raney Ni(W-2) In ethanol; water for 0.5h; Ambient temperature;	84%
With sodium hypophosphite; Raney-Ni (W-2) In ethanol; water for 0.5h; Ambient temperature; pH=5.2;	84%

(R)-1-p-Tolylsulfanyl-octan-2-ol → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With sodium hypophosphite; Raney Ni(W-2) In ethanol; water for 0.5h; Ambient temperature;	82%
With sodium hypophosphite; Raney-Ni (W-2) In ethanol; water for 0.5h; Ambient temperature; pH=5.2;	82%

rac-octan-2-ol (4128-31-8) → (S)-2-Octanol (6169-06-8) + (+/-)-2-octyl acetoacetate (143913-51-3)

Conditions	Yield
	A 77% B 75%

heptanal (111-71-7) + dimethyl zinc(II) (544-97-8) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
(1S,2R)-(-)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol In hexane 1.) r.t., 20 min; 2.) 0 deg C, 16 h;	70%

hexyl-methyl-ketone (111-13-7) → (S)-2-Octanol (6169-06-8) + (R)-Octan-2-ol (5978-70-1)

Conditions	Yield
With methanesulfonic acid; (R,R)-dihydroborate In hexane at -20℃; for 48h; Title compound not separated from byproducts;	A n/a B 68%
With hydrogen; tartaric acid-NaBr-mod. Raney nickel In tetrahydrofuran at 100℃; for 8h; Product distribution; enantioface hydrogenation with various carboxylic acids;
With hydrogen; TA-NaBr-MRNi In tetrahydrofuran at 60℃; under 66195.7 Torr; for 96h; Product distribution; RNi(prepared from 3.8 g of the alloy(Ni/Al=42/58))modified with 200 ml of aq. solution containing (R,R)-TA(2 g) and NaBr(12 g) at pH 3.2, 100 deg C for 1 h. hydrogenations of var. 2-alkanones, reactions at var. temperatures;

rac-octan-2-ol (4128-31-8) + benzeneacetic acid methyl ester (101-41-7) → (S)-2-Octanol (6169-06-8) + (R)-Octan-2-ol (5978-70-1) + (R)-2-octyl phenylacetate (92883-26-6) + hexyl-methyl-ketone (111-13-7)

Conditions	Yield
With [(C4Ph4COHOCC4Ph4)(μ-H)][(CO)4Ru2]; Novozym(R) 435; 2,4-dimethylpentan-3-one In toluene at 70℃; under 142.511 Torr; for 40h;	A n/a B n/a C 63% D n/a

(S)-N-(oct-2-yloxy)-pyridine-2(1H)-thione (1200233-00-6) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With tri-n-butyl-tin hydride In dichloromethane at 18℃; for 0.0333333h; Inert atmosphere; Photolysis; enantioselective reaction;	59%

rac-octan-2-ol (4128-31-8) → (S)-2-Octanol (6169-06-8) + (R)-Octan-2-ol (5978-70-1)

Conditions	Yield
With Candida antarctica lipase B; 1-(10-carboxydecyl)-3-methylimidazolium hexafluorophosphate; diisopropyl-carbodiimide In acetone at 40℃; for 2h; Resolution of racemate; Enzymatic reaction; enantioselective reaction;	A 51% B 35%
Title compound not separated from byproducts;
With sodium acetate In water at 40℃; enantioselective reaction;	A n/a B n/a

rac-octan-2-ol (4128-31-8) + 2F6P(1-)*C30H52N4O3(2+) → (S)-2-Octanol (6169-06-8) + C23H43N2O2(1+)*F6P(1-)

Conditions	Yield
With Candida antarctica lipase B In acetone at 35℃; for 3h; Resolution of racemate; Enzymatic reaction; enantioselective reaction;	A 51% B n/a

vinyl acetate (108-05-4) + rac-octan-2-ol (4128-31-8) → (S)-2-Octanol (6169-06-8) + (R)-2-octyl acetate (54712-18-4)

Conditions	Yield
With sol-gel encapsulated Candida antarctica lipase SP 525 at 20℃; for 17h;	A 50% B 47%
With 4 A molecular sieve; immobilized lipase PS In di-isopropyl ether at 30℃; for 15h;	A 49% B 48.7%
With immobilized lipase B from Candida antarctica In hexane at 32℃; for 1h; Resolution of racemate; Enzymatic reaction;	A 40% B 35%

(S)-N-(oct-2-yloxy)-4-methylthiazole-2(3H)-thione (1200233-16-4) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With tri-n-butyl-tin hydride In dichloromethane at 18℃; for 0.416667h; Inert atmosphere; Photolysis; enantioselective reaction;	50%

(R)-octan-2-yl methanesulfonate (56772-63-5) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With sulfuric acid In tetrahydrofuran for 19h; Heating;	46%

octan-2-yl acrylate (42928-85-8) → (S)-2-Octanol (6169-06-8) + (R)-2-octanyl acrylate (15754-49-1)

Conditions	Yield
With Lipase Amano AK at 20℃; for 72h; pH=7; aq. phosphate buffer; Enzymatic reaction;	A 42% B 43%

oct-1-ene (111-66-0) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
With oleic acid hydratase from Elizabethkingia meningoseptica A248L mutant; water; hexanoic acid In dimethyl sulfoxide at 25℃; for 144h; pH=6; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	22%

succinic acid methyl ester-(1-methyl-heptyl ester) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
bei der Verseifung; succinic acid methyl ester--ester;

malonic acid ethyl ester-(1-methyl-heptyl ester) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
Hydrolysis; malonic acid ethyl ester--ester;

succinic acid ethyl ester-(1-methyl-heptyl ester) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
bei der Verseifung; succinic acid ethyl ester--ester;

malonic acid bis-(1-methyl-heptyl ester) (89837-79-6) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
Hydrolysis; malonic acid di--ester;

bis(1-methylheptyl)butanedioate (29390-06-5) → (S)-2-Octanol (6169-06-8)

Conditions	Yield
bei der Verseifung; succinic acid di--ester;

(S)-2-Octanol (6169-06-8) + (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5, 20445-33-4) → (R)-2-octyl (R)-α-methoxy-α-trifluoromethylphenylacetate (20445-10-7)

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃;	100%

(S)-2-Octanol (6169-06-8) + acetic anhydride (108-24-7) → (S)-1-methylheptyl acetate (3540-05-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 13h;	99%
With pyridine	93.1%
for 1h; Heating;	82%
With dmap at 30℃; for 18h;
With dmap

(S)-2-Octanol (6169-06-8) → (R)-(-)-2-iodooctane (29117-48-4)

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane for 1h; Ambient temperature;	98%
With iodine In Petroleum ether for 6h; Heating;	25%
With hydrogen iodide

(S)-2-Octanol (6169-06-8) + methanesulfonyl chloride (124-63-0) → (S)-2-<(Methanesulfonyl)oxy>octane (62820-85-3)

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	98%
With pyridine for 2h;	86%
With triethylamine In dichloromethane at 15 - 20℃; for 1h;
With pyridine
With pyridine

(S)-2-Octanol (6169-06-8) + 2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) → (S)-2-octyl acetoacetate (143913-51-3)

Conditions	Yield
for 0.1h; microwave irradiation;	98%

(S)-2-Octanol (6169-06-8) + Acetylenedicarboxylic acid (142-45-0) → bis[(1S)-1-methylheptyl] acetylenedicarboxylate (1181217-27-5)

Conditions	Yield
With sulfuric acid In tetrahydrofuran for 14h; Reflux;	97%

(S)-2-Octanol (6169-06-8) + benzoic acid (65-85-0) → (S)-benzoic acid 1-methylheptyl ester (6938-51-8, 78687-05-5, 98819-31-9, 34881-29-3)

Conditions	Yield
With cyanomethylenetributyl-phosphorane In benzene at 100℃; for 24h;	96%

(S)-2-Octanol (6169-06-8) + 4-nitro-benzoic acid (62-23-7) → (1R)-1-methylheptyl 4-nitrobenzoate

Conditions	Yield
With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine In toluene at 20℃; Product distribution / selectivity; Mitsunobu reaction;	96%
With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine In toluene at 20℃; for 3.5h; Mitsunobu reaction; Inert atmosphere; stereospecific reaction;	96%
With ethyl 2-(3,4-dichlorophenyl)azocarboxylate; triphenylphosphine In toluene at 20℃; for 5h; Mitsunobu Displacement; Inert atmosphere;	93%

(S)-2-Octanol (6169-06-8) + 4,4'-Dihydroxybenzophenone (611-99-4) → 4,4’-bis[(R)-2-octyloxy]benzophenone

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 0 - 20℃; for 17.5h; Inert atmosphere;	96%

(S)-2-Octanol (6169-06-8) → (R)-2-chlorooctane (18651-57-5)

Conditions	Yield
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane 1.) 0 deg C; 2.) rt., 3h;	95%
With trichloroacetonitrile; triphenylphosphine In acetonitrile for 1h; Ambient temperature;	70%
With diethyl ether; phosphorus trichloride

(S)-2-Octanol (6169-06-8) + methyl 5-chloro-2-fluoro-4-hydroxy-benzoate (245743-64-0) → (R)-5-chloro-2-fluoro-4-(2-octyloxy)benzoate (211172-74-6)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 25℃; for 2h; Etherification;	95%

(S)-2-Octanol (6169-06-8) + ethyl acetoacetate (141-97-9) → (S)-2-octyl acetoacetate (143913-51-3)

Conditions	Yield
for 0.333333h; microwave irradiation;	95%

(S)-2-Octanol (6169-06-8) + p-toluenesulfonyl chloride (98-59-9) → (S)-1-methylheptyl tosylate (34817-25-9)

Conditions	Yield
With trimethylamine hydrochloride; triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere;	94%
With trimethylamine hydrochloride; triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere;	94%
With pyridine at 4℃; Inert atmosphere;	92%

(S)-2-Octanol (6169-06-8) + 4-(methoxycarbonyloxy)benzoic acid (14180-11-1) → 4-methoxycarbonyloxybenzoic acid (S)-1-methylheptyl ester (271786-19-7)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 48h;	94%

(S)-2-Octanol (6169-06-8) + methyl 4-hydroxylbenzoate (99-76-3) → methyl 4-{[(1R)-1-methylheptyl]oxy} benzoate (138705-74-5)

Conditions	Yield
Stage #1: (S)-2-Octanol; methyl 4-hydroxylbenzoate With triphenylphosphine In tetrahydrofuran at 0℃; for 0.25h; Mitsunobu reaction; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 0 - 20℃; for 8h; Mitsunobu reaction;	94%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran

(S)-2-Octanol (6169-06-8) + benzoic acid (65-85-0) → (R)-benzoic acid 1-methylheptyl ester (6938-51-8, 34881-29-3, 98819-31-9, 78687-05-5)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 20℃; Product distribution / selectivity; Mitsunobu reaction;	93%
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In benzene at 60℃; for 24h;	91%
With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine In diethyl ether at 20℃; for 2h; Mitsunobu reaction; Inert atmosphere; stereospecific reaction;	89%

(S)-2-Octanol (6169-06-8) + N,N-diethyl 4'-bromo-4-methoxybiphenyl-2-carboxamide (666829-99-8) → (R)-N,N-diethyl 4'-bromo-4-(1-methylheptyloxy)biphenyl-2-carboxamide (666830-01-9)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 25℃; for 4h; Mitsunobu reaction;	93%

(S)-2-Octanol (6169-06-8) + 4-{(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-oxo-butyric acid ethyl ester → 4-{(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-oxo-butyric acid (S)-1-methyl-heptyl ester

Conditions	Yield
In chlorobenzene for 0.5h; microwave irradiation;	92%

(S)-2-Octanol (6169-06-8) + 2-Iodobenzoyl chloride (609-67-6) → C15H21IO2 (1093198-58-3)

Conditions	Yield
	92%

(S)-2-Octanol (6169-06-8) + 4-Bromobenzoic acid (586-76-5) → (S)-1-methylheptyl 4-bromobenzoate (1160843-08-2)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	92%

4-nitro-phenol (100-02-7) + (S)-2-Octanol (6169-06-8) → (S)-4-(1-methylheptyl)oxy-1-nitrobenzene (850903-50-3)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 10 - 20℃; Inert atmosphere;	91%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 18h; Mitsunobu Displacement;	91%
With di-isopropyl azodicarboxylate; triphenylphosphine In diethyl ether at 0 - 20℃;	90%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran

(S)-2-Octanol (6169-06-8) + benzaldehyde (100-52-7) → ({[(1S)-1-methylheptyl]oxy}methyl)benzene

Conditions	Yield
With triethylsilane; ytterbium(III) triflate In 1,2-dichloro-ethane for 4h; Reflux;	91%
With triethylsilane; iron(III) chloride In nitromethane at 20℃; for 1h;	81%

Carbonyl fluoride (353-50-4) + (S)-2-Octanol (6169-06-8) → C9H17FO2

Conditions	Yield
With potassium fluoride In diethyl ether at 0℃;	90%

Upstream product

• 64-17-5 ethanol 
• 5978-55-2 (2R)-2-bromooctane 
• 15586-11-5 2-chlorocarbonyloxy-octane 
• 127-08-2 potassium acetate 
• 582-25-2 Potassium benzoate 
• 7214-62-2 nitrous acid-((S)-1-methyl-heptyl ester) 
• 88726-12-9 (2R,1'R,3'R)-2-(3'-hydroxy-1'-methylbutoxy)octane 
• 88764-88-9 (2S,1'R,3'R)-2-(3'-hydroxy-1'-methylbutoxy)octane 
• 3761-92-0 n-hexylmagnesium bromide 
• 75-07-0 acetaldehyde 
• 89583-95-9 Hexylmagnesiumiodid 
• 105087-04-5 (S)-(Z)-3-octen-2-ol 
• 71-43-2 benzene 
• 64226-59-1 sodium rac-2-ocyl sulfate 

Downstream Products

• 59078-33-0 octan-2-yl 3-phenylpropiolate 
• 15586-11-5 2-chlorocarbonyloxy-octane 
• 100879-95-6 (S)-chloro-(1-methyl-heptyloxy)-phenyl-borane 
• 109845-03-6 bis-((S)-1-methyl-heptyloxy)-phenyl-borane 
• 112867-61-5 ((S)-1-methyl-heptyloxy)-diphenyl-borane 
• 24848-81-5 (+)-tris{octyl⁽²⁾oxy}}borane 
• 101432-92-2 chloro-bis-((S)-1-methyl-heptyloxy)-borane 
• 693-16-3 (R)-2-octylamine 
• 5978-55-2 (2R)-2-bromooctane 
• 7598-65-4 (+)(S:S:S)-tris-(1-methyl-heptyl)-phosphite 
• 628-61-5 2-chlorooctane 
• 6938-51-8 (R)-benzoic acid 1-methylheptyl ester 
• 111153-20-9 (S)-(+)-1-methylheptyl 4-benzyloxybenzoate 
• 168073-39-0 (2R)-(2-methyl-1-methylthiooctyl)tolylsulfone 

Relevant articles and documents

Supported ionic liquid-like phases as efficient solid ionic solvents for the immobilisation of alcohol dehydrogenases towards the development of stereoselective bioreductions

Polymeric materials containing ionic liquid fragments, like those found in bulk ILs, are excellent solid media for the immobilisation of biocatalysts. Herein, the entrapment of the enzymatic system formed by alcohol dehydrogenase from Rhodococcus ruber (ADH-A) overexpressed in E. coli and its coenzyme has been studied. The activity, stability and reusability of these preparations have been investigated in the bioreduction of prochiral ketones finding excellent levels of conversion and selectivity. Interestingly, the immobilised enzyme remained active and exhibited excellent stability in aqueous solutions after several recycling uses. More importantly, these biopolymer materials retained most of their activity after consecutive reaction cycles, prolonged storage and under flow conditions.

Chiral Imidazo[1,5- a]pyridine-Oxazolines: A Versatile Family of NHC Ligands for the Highly Enantioselective Hydrosilylation of Ketones

Herein we report the synthesis and application of a versatile class of N-heterocyclic carbene ligands based on an imidazo[1,5-a]pyridine-3-ylidine backbone that is fused to a chiral oxazoline auxiliary. The key step in the synthesis of these ligands involves the installation of the oxazoline functionality via a microwave-assisted condensation of a cyano-azolium salt with a wide variety of 2-amino alcohols. The resulting chiral bidentate NHC-oxazoline ligands form stable complexes with rhodium(I) that are efficient catalysts for the enantioselective hydrosilylation of structurally diverse ketones. The corresponding secondary alcohols are isolated in good yields (typically >90%) with good to excellent enantioselectivities (80-93% ee). The reported hydrosilylation occurs at ambient temperatures (40 °C), with excellent functional group tolerability. Even ketones bearing heterocyclic substituents (e.g., pyridine or thiophene) or complex organic architectures are hydrosilylated efficiently, which is discussed further in this report.

Organic-inorganic nanocrystal reductase to promote green asymmetric synthesis

An acetophenone reductase from Geotrichum candidum (GcAPRD) was immobilized by the organic-inorganic nanocrystal method. The GcAPRD nanocrystal presented improved stability and recyclability compared with those of the free GcAPRD. Moreover, the GcAPRD nanocrystal reduced broad kinds of ketones with excellent enantioselectivities to produce beneficial chiral alcohols such as (S)-1-(3′,4′-dichlorophenyl)ethanol with >99% yield and >99% ee. The robust and versatile properties of the GcAPRD nanocrystal demonstrated an approach to promote green asymmetric synthesis and sustainable chemistry. This journal is