28079-04-1

Basic information

• Product Name: (Z)-8-DODECEN-1-YL ACETATE
• Synonyms: (8Z)-8-Dodecenyl acetate;(Z)-8-Dodecen-1-ol acetate;8-Dodecen-1-ol, acetate, (Z)-;acetate,(z)-8-dodecen-1-o;z-8-dodecenyl;z-8-dodecenylacetate;(Z)-8-DODECEN-1-YL ACETATE;CIS-8-DODECEN-1-OL ACETATE
• CAS NO: 28079-04-1
• Molecular Formula: C₁₄H₂₆O₂
• Molecular Weight: 226.36
• EINECS: 248-823-6
• Product Categories: insect pheromone
• Mol File: 28079-04-1.mol

Chemical Properties

• Boiling Point: 300.1 °C at 760 mmHg
• Flash Point: 96.5 °C
• Appearance: /
• Density: 0.881
• Vapor Pressure: 0.00114mmHg at 25°C
• Refractive Index: 1.448
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Water (Slightly)
• Stability: Very Hygroscopic
• CAS DataBase Reference: (Z)-8-DODECEN-1-YL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-8-DODECEN-1-YL ACETATE(28079-04-1)
• EPA Substance Registry System: (Z)-8-DODECEN-1-YL ACETATE(28079-04-1)

Safety Data

• Hazardous Substances Data: 28079-04-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-8-DODECEN-1-YL ACETATE is used as an active pharmaceutical ingredient for its antibacterial properties. It inhibits protein synthesis by binding to the L6 protein of the 50S ribosomal subunit, making it a potential candidate for the development of new antibiotics.
Used in Chemical Synthesis:
(Z)-8-DODECEN-1-YL ACETATE is used as a reagent for the synthesis of novel 1,2,3-triazole-1,4-benzoxazine hybrids, which exhibit antiproliferative activity. This application is particularly relevant in the development of new cancer treatments.
Used in Anti-Aging Applications:
(Z)-8-DODECEN-1-YL ACETATE is also used as a reagent in the synthesis of disubstituted isoxazoles, which have been shown to exhibit anti-aging activity. This makes it a valuable compound in the cosmetics and skincare industries for the development of anti-aging products.

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 675, 1973 DOI: 10.1016/S0040-4039(00)72431-2

InChI:InChI=1/C14H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h5-6H,3-4,7-13H2,1-2H3/b6-5-

Synthetic route

1-Acetoxydodec-8-yne (26906-26-3) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
With quinoline; hydrogen; Pd-BaSO4 In methanol	97%
With hydrogen; Lindlar's catalyst In hexane at 15℃;	7 g

(Z)-8-dodecenol (40642-40-8) + acetyl chloride (75-36-5) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
In pyridine	95%
With pyridine In benzene

Δ8-dodecen-1-ol (153123-34-3) + acetic anhydride (108-24-7) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
With pyridine at 5 - 25℃; for 2h; Large scale;	95%

(Z)-8-dodecenol (40642-40-8) + acetic anhydride (108-24-7) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 12h; Inert atmosphere; chemoselective reaction;	90%
With pyridine	89%
In pyridine for 24h; Ambient temperature;	75%

(Z)-1-(2-tetrahydropyranyloxy)dodec-8-ene (98398-50-6) + acetyl chloride (75-36-5) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
With acetic acid at 60℃; for 6h;	77%

1-penten (109-67-1) + non-8-en-1-yl acetate (13038-22-7) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
With C32H41N3O4Ru In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; Glovebox; chemoselective reaction;	65%
With C35H47N3O4Ru In tetrahydrofuran at 35℃; for 2h;	58%
With Z-selective metathesis catalyst
With Z-selective cross-metathesis catalyst Inert atmosphere;

Acetic acid (Z)-6-(toluene-4-sulfonyloxy)-dodec-8-enyl ester → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
With sodium tetrahydroborate In dimethyl sulfoxide at 80℃;	58%

(E)-8-dodecenyl acetate (38363-29-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
(i) HCl, (ii) NBS, (iii) NaI, DMF; Multistep reaction;

Δ8-dodecen-1-ol (153123-34-3) + acetic anhydride (108-24-7) → (Z)-8-dodecen-1-yl acetate (28079-04-1) + (E)-8-dodecenyl acetate (38363-29-0)

Conditions	Yield
With pyridine Yield given. Yields of byproduct given;
With pyridine at 5 - 25℃; for 2h; Overall yield = 93.3 %; Overall yield = 0.57 kg;	A n/a B n/a

acetic anhydride (108-24-7) + (Z)-1-(2-tetrahydropyranyloxy)dodec-8-ene (98398-50-6) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
With pyridine; water; toluene-4-sulfonic acid 1) MeOH, room temp., 15 h; 2) room temp., 24 h.; Yield given. Multistep reaction;

n-butyl(triphenyl)phosphonium bromide (1779-51-7) → (Z)-8-dodecen-1-yl acetate (28079-04-1) + (E)-8-dodecenyl acetate (38363-29-0)

Conditions	Yield
n-butyl(triphenyl)phosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 18℃; for 2h; Further stages. Title compound not separated from byproducts.;

1-Pentyne (627-19-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH / dimethylsulfoxide 2: LiAlH4 / diethyl ether 3: H2 / Lindlar catalyst / methanol 4: Py / benzene View Scheme

(Z)-oct-4-enal (39924-26-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions

Yield

Multi-step reaction with 4 steps 1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C 2: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h. 3: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 4: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

7-chloroheptanoic acid (821-57-8) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH / dimethylsulfoxide 2: LiAlH4 / diethyl ether 3: H2 / Lindlar catalyst / methanol 4: Py / benzene View Scheme

(Z)-4-octene-1-ol (54393-36-1) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h. 2: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 3: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

8-Dodecyn-1-ol (41589-71-3) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Lindlar catalyst / methanol 2: Py / benzene View Scheme
Multi-step reaction with 2 steps 1: 85 percent / H2 / Ni-P2 2: 89 percent / pyridine View Scheme
Multi-step reaction with 2 steps 1: 1) 9-borabicyclo<3.3.1>nonane, 2) CH3CO2H / 1) THF, 0 deg C, 24 h, 2) reflux, 9 h 2: pyridine / 15 h / 20 °C View Scheme

8-Dodecinsaeure (18545-07-8) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether 2: H2 / Lindlar catalyst / methanol 3: Py / benzene View Scheme

1,1-dimethoxy-8-tosyloxy-(4Z)-octene (82861-01-6) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions

Yield

Multi-step reaction with 6 steps 1: 85 percent / NaI, zinc dust / bis-(2-methoxy-ethyl) ether / 1.5 h / 65 - 70 °C 2: 95 percent / 5percent aq. HCl / acetone / 6 h / Ambient temperature 3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C 4: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h. 5: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 6: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

1,1-dimethoxy-4Z-octene (119265-28-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions

Yield

Multi-step reaction with 5 steps 1: 95 percent / 5percent aq. HCl / acetone / 6 h / Ambient temperature 2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C 3: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h. 4: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 5: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

(Z)-1-bromo-4-octene (79837-81-3) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 2: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

7-bromo-hept-1-ene (4117-09-3) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 89 percent / NH2 / tetrahydrofuran; dimethylsulfoxide 2: 1) 9-BBN, 2) H2O2, AcONa 3: 85 percent / H2 / Ni-P2 4: 89 percent / pyridine View Scheme

1-pentynyl lithium (18643-50-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 89 percent / NH2 / tetrahydrofuran; dimethylsulfoxide 2: 1) 9-BBN, 2) H2O2, AcONa 3: 85 percent / H2 / Ni-P2 4: 89 percent / pyridine View Scheme
Multi-step reaction with 6 steps 1: 69 percent / Fe acetylacetonate / diethyl ether; liquid ammonia / from -30 to 20 deg C, 15 h 2: 95 percent / pyridine / -5 - 0 °C 3: 90 percent / LiBr / acetone / 6 h / Heating 4: 78 percent / CuI, bi-2-pyridyl / tetrahydrofuran / 2 h / 2 °C 5: 1) 9-borabicyclo<3.3.1>nonane, 2) CH3CO2H / 1) THF, 0 deg C, 24 h, 2) reflux, 9 h 6: pyridine / 15 h / 20 °C View Scheme

Dodec-1-en-8-yne (197901-17-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) 9-BBN, 2) H2O2, AcONa 2: 85 percent / H2 / Ni-P2 3: 89 percent / pyridine View Scheme

6-acetoxy-1-hexanal (68750-25-4) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) BuSnCl3 / 1.) CHCl3, 0 deg C, 2 min, 2.) CHCl3, 0 deg C, 30 min 2: DMPA / CH2Cl2 3: 58 percent / NaBH4 / dimethylsulfoxide / 80 °C View Scheme

hex-2-enyl-tributylstannane (74940-39-9) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) BuSnCl3 / 1.) CHCl3, 0 deg C, 2 min, 2.) CHCl3, 0 deg C, 30 min 2: DMPA / CH2Cl2 3: 58 percent / NaBH4 / dimethylsulfoxide / 80 °C View Scheme

Acetic acid (Z)-6-hydroxy-dodec-8-enyl ester (156360-24-6) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: DMPA / CH2Cl2 2: 58 percent / NaBH4 / dimethylsulfoxide / 80 °C View Scheme

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran (53963-10-3) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: KO-tBu, n-BuLi / hexane; diethyl ether / -78 deg C up to RT for 17 h 2: 1.) ICl; 2.) aq. KF / 1.) CCl4, 15 min; 2.) DMSO, RT, 4 h 3: 88 percent / (Ph3P)4Pd / tetrahydrofuran / Ambient temperature 4: 77 percent / HOAc / 6 h / 60 °C View Scheme

(Z)-9-iodo-1-(2-tetrahydropyranyloxy)non-8-ene (98369-16-5) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / (Ph3P)4Pd / tetrahydrofuran / Ambient temperature 2: 77 percent / HOAc / 6 h / 60 °C View Scheme

9-trimethylsilyl-1-(2-tetrahydropyranyloxy)-8-(E)-nonene (98369-07-4) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) ICl; 2.) aq. KF / 1.) CCl4, 15 min; 2.) DMSO, RT, 4 h 2: 88 percent / (Ph3P)4Pd / tetrahydrofuran / Ambient temperature 3: 77 percent / HOAc / 6 h / 60 °C View Scheme

methanol (67-56-1) + (Z)-8-dodecen-1-yl acetate (28079-04-1) → Acetic acid 8-methoxy-dodecyl ester + Acetic acid 9-methoxy-dodecyl ester

Conditions	Yield
With sodium tetrahydroborate; mercury(II) diacetate 1.) 48 h, RT; 2.) glacial acetic acid; Multistep reaction;

Dimethyldisulphide (624-92-0) + (Z)-8-dodecen-1-yl acetate (28079-04-1) → Acetic acid 8,9-bis-methylsulfanyl-dodecyl ester (84801-35-4)

Conditions	Yield
With iodine In diethyl ether; hexane at 40℃;

Upstream product

• 38363-29-0 (E)-8-dodecenyl acetate 
• 40642-40-8 (Z)-8-dodecenol 
• 75-36-5 acetyl chloride 
• 26906-26-3 1-Acetoxydodec-8-yne 
• 153123-34-3 Δ⁸-dodecen-1-ol 
• 108-24-7 acetic anhydride 
• 98398-50-6 (Z)-1-(2-tetrahydropyranyloxy)dodec-8-ene 
• 1779-51-7 n-butyl(triphenyl)phosphonium bromide 
• 39924-26-0 (Z)-oct-4-enal 
• 821-57-8 7-chloroheptanoic acid 
• 54393-36-1 (Z)-4-octene-1-ol 
• 41589-71-3 8-Dodecyn-1-ol 
• 82861-01-6 1,1-dimethoxy-8-tosyloxy-(4Z)-octene 
• 197901-17-0 Dodec-1-en-8-yne 

Relevant articles and documents

PHEROMONES OF INSECTS AND THEIR ANALOGS. XXI. SYNTHESIS OF ALK-8Z-EN-1-OLS AND THEIR ACETATES FROM A FUNCTIONALLY DIFFERENTIATED PRODUCT OF OZONOLYSIS OF CYCLOOCTENE

Dodec-8Z-en-1-ol (VIII) and tetradec-8Z-en-1-ol (IX) and the corresponding acetates (X and IX) - components of the sex pheromones of many species of Lepidoptera - have been synthesized from cyclooctene (I) in three stages.The ozonolysis of (I) ( -70 deg C, CH2Cl2-MeOH), NaHCO3; -20 deg C, Ac2O/Et3N) led to methyl 8-oxooctanoate (II).The DNPH of (II), (III), mp 59-61 deg C.The coupling of (II) with n-C3H17CH=PPh3 (IV) or with n-C5H11CH=PPh3 (V) (-70 deg C , 2h; 25 deg C, 15h, Ar) gave the methyl esters of dodec-8Z-enoic (VI) and tetradec-8Z-enoic (VII) acids, respectively.The reduction of (VI) and (VII) gave the corresponding alcohols (VIII) and (IX) by the acetylation (Ac2O-Py, 25 deg C, 24h) of which, (X) and (XI) , were obtained.The yields (percent): (II) 80, (VI) 45, (VII) 60, (VIII) 95, (IX) 90, (X) 75, (XI) 74.The IR and PMR spectra of compounds (II) and (VI-XI) are given.

SYNTHESIS OF PHEROMONE DERIVATIVES VIA Z-SELECTIVE OLEFIN METATHESIS

Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

SYNTHESIS OF STRAIGHT-CHAIN LEPIDOPTERAN PHEROMONES THROUGH ONE- OR TWO- CARBON HOMOLOGATION OF FATTY ALKENES

Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.

Synthesis method of (Z/E)-8-dodecen-1-alcohol acetate compound

The invention provides a synthesis method of a (Z/E)-8-dodecane-1-alcohol acetate compound. Specifically, the method includes the following steps: preparing 8-bromooctanol from 1,8-octanediol, then performing esterification reaction to obtain 8-Bromooctanol acetate, and then preparing omega-acetoxyoctanyl triphenyl phosphine bromide salt, and finally performing reaction through Scholoer-wittig toobtain (Z/E)-8-dodecene-1-alcohol acetate. The synthesis method has the advantages of high availability of raw materials, high yield and good selectivity, and is suitable for industrial production.

SYNTHESIS OF PHEROMONES AND RELATED MATERIALS VIA OLEFIN METATHESIS

Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.

A (Z/E) - 8 - dodecene -1 - ethoxylate ester synthesis method

The invention discloses a (Z/E)-8-dodecylene-1-olacetate synthesis method. The method is characterized in that 1-halogenated pentine and magnesium 1-(2-oxotetrahydropyranyl)heptylhalide as initial raw materials undergo a coupling reaction to produce 8-(2-oxotetrahydropyranyl)dodecyne, the 8-(2-oxotetrahydropyranyl)dodecyne is subjected to hydrogenation, one-pot deprotection and esterification so that (Z)-8-dodecylene-1-olacetate and (E)-8-dodecylene-1-olacetate are obtained, wherein a mole ratio of (Z)-8-dodecylene-1-olacetate to (E)-8-dodecylene-1-olacetate is (90%-99.5%): (10%-0.5%). The method utilizes 1-halogenated pentine and magnesium 1-(2-oxotetrahydropyranyl)heptylhalide as initial raw materials, provides a novel reaction route, has a short route, produces less by-product, has simple and routine processes, is free of complex post-reaction treatment processes and improves production efficiency. The method satisfies different insect pheromone trap or lure requirements on an isomer ratio in practical application and is suitable for large-scale industrial production.

A pheromone food heart insectthe pear is small (Z/E)-8-dodecene acetum acid ester synthetic method

The invention provides a synthesis method of grapholitha molesta sex pheromone (Z/E)-8-dodecene acetate. The synthesis method comprises the following steps: (1) by taking methylbenzene or benzene as a solvent and 1,8-octanediol and hydrobromic acid as starting raw materials, performing unilateral bromination reaction to obtain 8-bromooctanol; (2) by taking ethanol as a solvent, adding 8-bromooctanol and triphenylphosphine into a reaction kettle, after the reaction, cooling and separating out 8-hydroxyl octyl triphenylphosphine crystals by taking methylbenzene as an eluent; (3) performing Witting reaction on the 8-hydroxyl octyl triphenylphosphine and n-butyraldehyde under the presence of a catalyst 18-crown ether-6 to obtain (Z/E)-8-dodeceneanol, wherein potassium carbonate is adopted as alkali; and (4) by taking pyridine as a solvent, reacting the (Z/E)-8-dodeceneanol with acetic anhydride or acetyl chloride to obtain (Z/E)-8-dodecene acetate. The method mild in conditions, fewer in steps, high in yield, and suitable for industrial production, and raw materials are easily available.

Palladium-catalyzed decarbonylative dehydration of fatty acids for the production of linear alpha olefins

A highly efficient palladium-catalyzed decarbonylative dehydration reaction of carboxylic acids is reported. This method transforms abundant and renewable even-numbered natural fatty acids into valuable and expensive odd-numbered alpha olefins. Additionally, the chemistry displays a high functional group tolerance. The process employs a low loading of palladium catalyst and proceeds under solvent-free and relatively mild conditions.

PALLADIUM-CATALYZED DECARBONYLATION OF FATTY ACID ANHYDRIDES FOR THE PRODUCTION OF LINEAR ALPHA OLEFINS

The present invention is directed to methods of forming olefins, especially linear alpha olefins from fatty acids or anhydrides, each method comprising: contacting an amount of precursor carboxylic acid anhydride with a palladium catalyst comprising a bidentate bis-phosphine ligand in a reaction mixture so as to form an olefin in a product with the concomittant formation and removal of CO and water from the reaction mixture, either directly or indirectly, wherein the reaction mixture is maintained with a sub-stoichiometric excess of a sacrificial carboxylic acid anhydride, an organic acid, or both, said sub-stoichiometric excess being relative to the amount of the precursor carboxylic acid anhydride. The precursor carboxylic acid anhydride may be added to the reaction mixture directly or formed in situ by the reaction between at least one precursor carboxylic acid with a stoichiometric amount of the sacrificial acid anhydride.

SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES

The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.