56683-54-6

Basic information

• Product Name: (Z)-hexadec-11-en-1-ol
• Synonyms: (Z)-hexadec-11-en-1-ol;cis-11-Hexadecanol;(Z)-11-HEXADECENOL;(11Z)-11-Hexadecen-1-ol;(Z)-11-Hexadecen-1-ol;11Z-16OH;11-Hexadecen-1-ol,(11Z)-;11Z-Hexadecen-1-ol
• CAS NO: 56683-54-6
• Molecular Formula: C16H32O
• Molecular Weight: 240.42468
• EINECS: 260-337-6
• Mol File: 56683-54-6.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 309°C at 760 mmHg
• Flash Point: 134.9°C
• Appearance: /
• Density: 0.847±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 5.97E-05mmHg at 25°C
• Refractive Index: 1.4608 (20℃)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 15.20±0.10(Predicted)
• CAS DataBase Reference: (Z)-hexadec-11-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-hexadec-11-en-1-ol(56683-54-6)
• EPA Substance Registry System: (Z)-hexadec-11-en-1-ol(56683-54-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 56683-54-6(Hazardous Substances Data)

Usage

Uses

(Z)-Hexadec-11-en-1-ol is a pheromone antagonist that regulates optimal mating time in moth Helicoverpa armigera.

Hazard

Low toxicity by ingestion.

InChI:InChI=1/C16H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h5-6,17H,2-4,7-16H2,1H3/b6-5-

Synthetic route

(Z)-11-hexadecen-1-yl acetate (34010-21-4) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Heating;	97%
Hydrolysis;
With Tris-HCl buffer; antennal esterase from Sesamia nonagrioides In ethanol at 32℃; for 1h; pH=8.0; Enzyme kinetics;

(11Z)-hexadec-11-enoic acid (2416-20-8) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 5h;	96%

11-hexadecyn-1-ol (65686-49-9) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; isobutylmagnesium bromide	92%
With sodium tetrahydroborate; Ni(CH3CO2)4H2O; hydrogen; diethylamine In ethanol	91%
With hydrogen; P2Ni	87%

(Z)-2-(hexadec-11-en-1-yloxy)tetrahydro-2H-pyran (99159-89-4) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With pyridinium p-toluenesulfonate In ethanol at 80℃;	92%
With pyridinium p-toluenesulfonate In methanol at 55℃; for 6h;	52%
With hydrogenchloride In methanol

1-hexene (592-41-6) + 11-eicosenol (68760-58-7) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With C32H41N3O4Ru In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox; chemoselective reaction;	76%

tetrakis(11-hydroxyundecyl)phosphanium bromide → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With polytetrafluoroethylene; pentanal; sodium ethanolate In tetrahydrofuran at 90 - 95℃; for 24h;	75%

(Z)-hexadec-5-ene (69820-25-3) → (Z)-11-hexadecen-1-ol (56683-54-6) + Δ5-hexadecenol (106463-48-3)

Conditions	Yield
With CYP52A13 hydroxylase enzyme; oxygen In water at 30℃; Reagent/catalyst;	A 74.4% B 27.6%
With CYP52A3 hydroxylase enzyme; oxygen In water at 30℃; Reagent/catalyst;	A 33.2% B 66.8%

1,11-hexadecadiene → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; ethyl acetate; calcium chloride In tetrahydrofuran 1.) reflux, 12 h then rt., 48 h; 2.) reflux, 7 h; 3.) 1.5 h;	68%
With sodium hydroxide; calcium borohydride; dihydrogen peroxide; ethyl acetate In tetrahydrofuran for 7h; Product distribution; Mechanism; Heating; var. alkene, metal borohydride;	68%

pentanal (110-62-3) + (11‑hydroxyundecyl)triphenylphosphonium bromide (19101-00-9) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Stage #1: (11‑hydroxyundecyl)triphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: pentanal In tetrahydrofuran at 20℃; for 24h;	54%
With sodium amide 1.) THF, 25 deg C, 30 min, 2.) -80 deg C to 25 deg C, 15 min; Yield given. Multistep reaction;

(11Z)-hexadeca-1,11-diene (65734-21-6, 82294-54-0) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide 1. THF, r.t., 5 h, 2. r.t., 17 h; Yield given. Multistep reaction;

pentanal (110-62-3) + (11‑hydroxyundecyl)triphenylphosphonium bromide (19101-00-9) → (Z)-11-hexadecen-1-ol (56683-54-6) + trans-11-hexadecen-1-ol (61301-56-2)

Conditions	Yield
With sodium hydride; dimethyl sulfoxide In tetrahydrofuran for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(Z)-11-hexadecenal (53939-28-9) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃; for 2h;	0.91 g
With lithium aluminium tetrahydride
With sodium tetrahydroborate In methanol at 20℃; for 1h;

(11Z)-hexadecenoic acid methyl ester (822-05-9) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 3h; Heating;

7-bromo-1-(1-ethoxy)ethoxyheptane (71570-81-5) + 1-tosyloxynon-4Z-ene (83165-98-4) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multistep reaction;

hexadec-11-ynal (86426-73-5) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With 9-borabicyclo[3.3.1]nonane dimer; acetic acid 1.) THF, 0-5 deg C, 24 h, 2.) reflux, 9 h; Multistep reaction;

10-chlorodecanol (51309-10-5) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) lithium amide / 1.) HMPTA, RT, 1.5 h, 2.) HMPTA, 25 deg C, 8 h 2: 91 percent / NaBH4, diethylamine, Ni(CH3CO2)4H2O, hydrogen / ethanol View Scheme

hex-1-yne (693-02-7) + [Co2(CO)8] → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) lithium amide / 1.) HMPTA, RT, 1.5 h, 2.) HMPTA, 25 deg C, 8 h 2: 91 percent / NaBH4, diethylamine, Ni(CH3CO2)4H2O, hydrogen / ethanol View Scheme

1-hexynyllithium (17689-03-1) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: HMPA / tetrahydrofuran 2: p-toluenesulfonic acid / methanol 3: H2 / Pd/BaSO4 View Scheme
Multi-step reaction with 3 steps 1: 85 percent 2: 1) O3, 2) NaBH4 / 1) cyclohexane, MeOH 3: 92 percent / i-BuMgBr, Cp2TiCl2 View Scheme

1-bromo-10-(tetrahydropyranyloxy)decane (51795-88-1) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: HMPA / tetrahydrofuran 2: p-toluenesulfonic acid / methanol 3: H2 / Pd/BaSO4 View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere 1.2: 16 h / Reflux 2.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 3.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere 1.2: 16 h / Inert atmosphere; Reflux 2.1: potassium hydroxide; N,N-dimethyl-formamide / 6 h / 145 °C / Inert atmosphere; Sealed tube 3.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C View Scheme

2-(hexadec-11-yn-1-yloxy)tetrahydro-2H-pyran (73784-65-3) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid / methanol 2: H2 / Pd/BaSO4 View Scheme
Multi-step reaction with 2 steps 1: p-TsOH / methanol 2: 87 percent / H2 / P2Ni View Scheme
Multi-step reaction with 2 steps 1: 5% Pd/C; hydrogen; quinoline / pentane / 18 h / 0 - 20 °C 2: toluene-4-sulfonic acid / methanol / 0.5 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 2: toluene-4-sulfonic acid / methanol / 16 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide; N,N-dimethyl-formamide / 6 h / 145 °C / Inert atmosphere; Sealed tube 2: toluene-4-sulfonic acid / methanol / 16 h / 20 °C View Scheme

1-undecen-11-ylbromide (7766-50-9) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent 2: 1) O3, 2) NaBH4 / 1) cyclohexane, MeOH 3: 92 percent / i-BuMgBr, Cp2TiCl2 View Scheme

heptadec-1-en-12-yne (114971-83-4) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) O3, 2) NaBH4 / 1) cyclohexane, MeOH 2: 92 percent / i-BuMgBr, Cp2TiCl2 View Scheme
Multi-step reaction with 2 steps 1: 1.) 2percent O3 in O2; 2.) sodium tetrahydroborate / 1.) cyclohexane, methanol; 2.) room temp., 15 h 2: 1.) isobutylmagnesium bromide; 2.) C5H5TiCl2 / 1.) diethyl ether, 0 deg C, 15 min; 2.) room temp., 1-1,5 h View Scheme

1-Bromo-11-hydroxyundecane (1611-56-9) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / acetonitrile 2: DMSO, NaH / tetrahydrofuran / 0.5 h View Scheme
Multi-step reaction with 2 steps 1.1: acetonitrile / 48 h / Inert atmosphere; Reflux 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 24 h / 20 °C View Scheme

(Z)-4-nonen-1-ol (59499-28-4) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / 6.5 h / -5 - 0 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine 2: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 3: pyridinium p-toluenesulfonate / ethanol / 80 °C View Scheme

(Z)-4-Nonenyl acetate (Z)-3-Nonenyl acetate (Z)-3-Nonenyl acetate (Z)-3-Nonenyl acetate (Z)-3-nonenyl acetate (83165-97-3) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 54 percent / KOH / H2O; methanol / 24 h / Ambient temperature 2: 95 percent / 6.5 h / -5 - 0 °C View Scheme

9-Decen-1-ol (13019-22-2) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / Ambient temperature 3: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) methanol, glacial acetic acid / 1.) THF, 0 deg C, 48 h, 2.) 25 deg C, 1 h 4: 97 percent / 10percent aq. sodium hydroxide / ethanol / 1 h / Heating View Scheme

9-decen-1-yl acetate (50816-18-7) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 3 steps 2: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) methanol, glacial acetic acid / 1.) THF, 0 deg C, 48 h, 2.) 25 deg C, 1 h 3: 97 percent / 10percent aq. sodium hydroxide / ethanol / 1 h / Heating View Scheme

Hexadec-11-ynyl acetate (53596-80-8) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) methanol, glacial acetic acid / 1.) THF, 0 deg C, 48 h, 2.) 25 deg C, 1 h 2: 97 percent / 10percent aq. sodium hydroxide / ethanol / 1 h / Heating View Scheme

hexenylmagnesium bromide (32359-01-6) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions

Yield

Multi-step reaction with 5 steps 1: diethyl ether / 4 h / 0 - 2 °C 2: 79 percent / pyridine / 1.) -5 deg C, 6 h; 2.) 0 deg C, 12 h 3: 53 percent / sodium iodide, zinc dust / tetrahydrofuran / 1.) 65-70 deg C, 3 h; 2.) 20 deg C, 3 h 4: 1.) 2percent O3 in O2; 2.) sodium tetrahydroborate / 1.) cyclohexane, methanol; 2.) room temp., 15 h 5: 1.) isobutylmagnesium bromide; 2.) C5H5TiCl2 / 1.) diethyl ether, 0 deg C, 15 min; 2.) room temp., 1-1,5 h View Scheme

(Z)-11-hexadecen-1-ol (56683-54-6) + acetyl chloride (75-36-5) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
With pyridine In benzene for 4h; Heating;	98.5%

(Z)-11-hexadecen-1-ol (56683-54-6) + acetic anhydride (108-24-7) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
With pyridine for 12h; Ambient temperature;	98%
With pyridine at 0℃; for 3h;	97%
With triethylamine In dichloromethane at 20℃; for 8h; Inert atmosphere; Schlenk technique; Cooling with ice;	94%

(Z)-11-hexadecen-1-ol (56683-54-6) → (Z)-11-Hexadecenyl bromide (80763-04-8)

Conditions	Yield
With pyridine; bromine; triphenylphosphine In dichloromethane at -30 - 20℃;	96%
Bromination;
Multi-step reaction with 2 steps 1: 85 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 2: 64 percent / LiBr / acetone / 3 h / Heating View Scheme

(Z)-11-hexadecen-1-ol (56683-54-6) → (Z)-11-hexadecenal (53939-28-9)

Conditions	Yield
Stage #1: (Z)-11-hexadecen-1-ol With oxalyl dichloride In dichloromethane; dimethyl sulfoxide at -78℃; for 0.333333h; Swern Oxidation; Inert atmosphere; Stage #2: With triethylamine In dichloromethane; dimethyl sulfoxide at -78 - 20℃; Inert atmosphere; chemoselective reaction;	95%
With Pyr*CrO3*HCl In dichloromethane for 2h; Ambient temperature;	93%
With sodium hypochlorite; TEMPOL; tetra(n-butyl)ammonium hydrogensulfate In toluene at 20 - 22℃; for 0.158333h; Reagent/catalyst; Temperature;	85%

dichloro-acetic acid (79-43-6) + (Z)-11-hexadecen-1-ol (56683-54-6) → Z-11-hexadecenyl-2,2-dichloroacetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide Acylation;	92%

(Z)-11-hexadecen-1-ol (56683-54-6) + methanesulfonyl chloride (124-63-0) → (Z)-hexadec-11-enyl methanesulfonate (107097-24-5)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.666667h;	90%
With triethylamine In dichloromethane at 20℃; for 1.5h;	85%

Difluoroacetic acid (381-73-7) + (Z)-11-hexadecen-1-ol (56683-54-6) → Z-11-hexadecenyl-2,2-difluoroacetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide Acylation;	88%

(Z)-11-hexadecen-1-ol (56683-54-6) + chloroacetic acid (79-11-8) → Z-11-hexadecenylmono-2-chloroacetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide Acylation;	85%

(Z)-11-hexadecen-1-ol (56683-54-6) + ethylene glycol (107-21-1) → 11-hexadecyn-1-ol (65686-49-9)

Conditions	Yield
With sodium hydroxide; bromine	80%

(Z)-11-hexadecen-1-ol (56683-54-6) + bromoacetic acid (79-08-3) → Z-11-hexadecenylmono-2-bromoacetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide Acylation;	77%

Fluoroacetic acid (144-49-0) + (Z)-11-hexadecen-1-ol (56683-54-6) → (Z)-11-Hexadecenyl fluoroacetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide Acylation;	69%

(Z)-11-hexadecen-1-ol (56683-54-6) + Trichloroacetyl chloride (76-02-8) → (Z)-11-Hexadecenyl trichloroacetate

Conditions	Yield
With pyridine Acylation;	69%

(Z)-11-hexadecen-1-ol (56683-54-6) + trifluoroacetic anhydride (407-25-0) → Z-11-hexadecenyl-2,2,2-trifluoroacetate

Conditions	Yield
With pyridine Acylation;	49%

(Z)-11-hexadecen-1-ol (56683-54-6) + N-formylimidazole (3197-61-3) → (Z)-11-hexadecenyl formate (65202-09-7)

Conditions	Yield
With imidazolyl sodium In tetrahydrofuran at 70℃; for 3h;

(Z)-11-hexadecen-1-ol (56683-54-6) → 10-((2S,3R)-3-Butyl-oxiranyl)-decan-1-ol

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 24h;

Upstream product

• 2416-20-8 (11Z)-hexadec-11-enoic acid 
• 71570-81-5 7-bromo-1-(1-ethoxyethoxy)heptane 
• 83165-98-4 1-tosyloxynon-4Z-ene 
• 693-02-7 hex-1-yne 
• 73784-65-3 2-(hexadec-11-yn-1-yloxy)tetrahydro-2H-pyran 
• 35289-31-7 dodec-11-en-1-ol 
• 5675-51-4 1,12-dodecandiol 
• 111-81-9 Methyl 10-undecenoate 
• 6287-90-7 11-bromo-undecanoic acid methyl ester 
• 24724-07-0 methyl 11-hydroxyundecanoate 
• 42236-50-0 1,12-diacetoxydodecane 
• 112-41-4 1-dodecene 
• 765-03-7 1-dodecyne 
• 112-29-8 1-bromo dodecane 

Downstream Products

• 53939-28-9 (Z)-11-hexadecenal 
• 34010-21-4 (Z)-11-hexadecen-1-yl acetate 
• 1256266-69-9 C₂₂H₃₆S 
• 65686-49-9 11-hexadecyn-1-ol 
• 884843-10-1 C₃₉H₆₈O₂S 
• 884843-04-3 (5Z,25Z)-17-benzenesulfonyl-5,25-hentriacontadiene 

Relevant articles and documents

Stereoselective hydrogenation of 11-hexadecyne-1-ol on supported copper catalysts

Hydrogenation of 11-hexadecyne-1-ol on 5-30 % copper catalysts supported on γ-Al2O3 and MgCO3 results in as-11-hexadecene-1-ol in 100 % yield. Hydrogenation does not occur on 5-30 % Cu/ZnO catalysts. The difference in behavior of the catalysts is connected with the valent state of copper on the surface and different hydrogen chemisorption.

Palladium nanoparticlesin situsynthesized onCyclea barbatapectin as a heterogeneous catalyst for Heck coupling in water, the reduction of nitrophenols and alkynes

This study develops an effective method for thein situsynthesis of palladium nanoparticles (PdNPs) usingCyclea barbatapectin as a green reducing and stabilizing reagent. The PdNP@pectin nanocomposite was well characterized by analysis techniques such as UV-vis, FTIR, EDX, XRD, SEM, HR-TEM and STEM-mapping. Crystalline PdNPs were found to be distributed in the size range of 1-25 nm with the highest frequency of 6-12 nm. PdNP@pectin exhibited excellent recyclable catalysis activity for the Heck coupling reaction in water medium. The kinetics and recyclability of nanoparticles were investigated for the catalytic reduction ofo-,m- andp-nitrophenol. The result showed a good catalysis efficiency with five successful recycles without compromising much. In particular, the nanocomposite was used as a catalyst for the conversion of alkynes intocis-alkenes with KOH/DMF as a hydrogenation source. The reaction was also utilized effectively for the synthesis of sex pheromones, includingPlutella xylostella((Z)-11-hexadecen-1-yl acetate) andCylas formicarius((Z)-3-dodecen-1-yl(E)-2-butenoate) with the total yields of 70% and 68%, respectively. Therefore, PdNPs supported onC. barbatapectin are promising catalysis materials for application in various fields.

Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)

Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.

A moth pheromone synthesis method of pickles (by machine translation)

The invention belongs to the technical field of chemical synthesis, in particular relates to a moth pheromone of the pickles synthetic method, comprises the following steps: 1) in the organic solvent, 11 - bromo - 1 - [...] with triphenylphosphine reaction to produce bromo Hendecane [...]; 2) under the protection of nitrogen, step 1) obtained in the bromo Hendecane [...] with valeraldehyde, sodium ethoxide in tetrahydrofuran solvent to react to generate cis - 11 - sixteen-carbon vinyl alcohol; 3) in the dichloromethane solution in, step 2) obtained in the cis - 11 - sixteen carbon alcohol with the occurrence chloro-chromic acid pyridine salt to the oxidizing reaction to produce cis - 11 - sixteen [...]; 4) in dichloromethane in, step 2) obtained in the cis - 11 - sixteen carbon alcohol with acetic anhydride, pyridine reaction to produce cis - 11 - sixteen-carbon vinyl alcohol acetate. The invention uses inexpensive and easily obtained 11 - bromo - 1 - [...] as the starting material, the synthesis step is reduced, simplifies the synthesis process, the product yield is high, the reaction conditions are mild and controllable, low requirements on equipment, can be used for industrial production. (by machine translation)