53042-79-8

Basic information

• Product Name: HEXADECADIENOLACETATE
• Synonyms: HEXADECADIENOLACETATE;(Z,E)-7,11-HEXADECADIEN-1-YLACETATE;(7Z,11E)-7,11-Hexadecadien-1-ol acetate;(Z,E)-Gossyplure;7,11-Hexadecadien-1-yl Acetate(mixture of (Z)-,(E)-);7Z11E-16Ac;cis-7,trans-11-Hexadecadienyl acetate;(7Z,11E)-Hexadecadien-1-yl acetate
• CAS NO: 53042-79-8
• Molecular Formula: C₁₈H₃₂O₂
• Molecular Weight: 280.45
• Mol File: 53042-79-8.mol

Chemical Properties

• Melting Point: <25℃
• Boiling Point: 181℃ (1 Torr)
• Flash Point: 102.1°C
• Appearance: /
• Density: 1.0035 (rough estimate)
• Refractive Index: 1.4610 (20℃)
• CAS DataBase Reference: HEXADECADIENOLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: HEXADECADIENOLACETATE(53042-79-8)
• EPA Substance Registry System: HEXADECADIENOLACETATE(53042-79-8)

Safety Data

• Hazardous Substances Data: 53042-79-8(Hazardous Substances Data)

Synthetic route

(E)-11-hexadecen-7-ynyl acetate (53042-78-7) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
With quinoline; hydrogen; Lindlar's catalyst In ethanol under 760 Torr;	94%
With quinoline; hydrogen; Lindlar's catalyst In methanol

(7Z,11E)-1-(2'-tetrahydropyranyloxy)hexadeca-7,11-diene (53155-14-9) + acetyl chloride (75-36-5) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
With acetic acid Heating;	92%
In acetic acid for 5h; Heating;	81%
With pyridine; acetic acid for 12h; Ambient temperature;	80%
In acetic acid

(7Z,11E)-hexadeca-7,11-dien-1-ol (53963-09-0) + acetic anhydride (108-24-7) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
With pyridine	62%
With pyridine
With pyridine for 24h; Ambient temperature; Yield given;

ethyl 3-hydroxy-heptanoate (126784-39-2) + Acetic acid (Z)-10-iodo-dec-7-enyl ester → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multistep reaction;

11-(Z/E)-Hexadecen-7-yn-1-yl acetate (53042-78-7, 53042-80-1) → (7Z,11Z)-7,11-hexadecadien-1-yl acetate (52207-99-5) + 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
With quinoline; hydrogen; Pd-BaSO4 In methanol under 3800 Torr; Ambient temperature; Yield given. Yields of byproduct given;

2-[((7Z,11Z)-Hexadeca-7,11-dienyl)oxy]-tetrahydro-pyran (53155-14-9, 53155-15-0, 53155-16-1, 53155-17-2) + acetyl chloride (75-36-5) → (7Z,11Z)-7,11-hexadecadien-1-yl acetate (52207-99-5) + 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
In acetic acid for 0.5h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
In acetic acid for 3h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

7,11-hexadecadienal (96883-53-3, 96883-54-4, 131392-75-1, 131400-46-9) + acetyl chloride (75-36-5) → (7Z,11Z)-7,11-hexadecadien-1-yl acetate (52207-99-5) + 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
In pyridine at 0℃; for 0.166667h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

acetic acid 7-oxo-heptyl ester (29425-54-5) + <(E)-4-Nonenyl>-triphenylphosphonium-bromid (59512-90-2) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8) + (7Z,11Z/E)-7,11-hexadecadienyl acetate (53042-81-2)

Conditions	Yield
With sodium hexamethyldisilazane 1.) THF, RT, 1 h, 2.) THF, from -60 to -50 deg C, 6 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran (53963-10-3) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1) LiNH2 / 1) NH3(l), 3 h; 2) abs THF, 20-25 deg C, 13 h. 2: 80 percent / nickel acetate, NaBH4, ethylene diamine / ethanol 3: 80 percent / pyridinium chlorochromate / CH2Cl2 4: 1) butyllithium, 2) butyllithium, 3) ethanol / 1) abs. THF, hexan, -30 deg C, 90 min; 2) abs. THF, hexan, 40 min at -60 deg C and 15 min at -30 deg C; 3) 30 min at -30 deg C and 24 h at -40 deg C. 5: 92 percent / glacial acetic acid / Heating View Scheme
Multi-step reaction with 5 steps 1: 76 percent / LiNH2, NH3 (liquid) / tetrahydrofuran / 5 h 2: ethylene diamine, H2 / Ni(OAc)2.4H2O, NaBH4 / ethanol; H2O 3: 90 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 4: 1.) n-BuLi / 1.) ether, hexane, RT, 1 h; 2.) ether, hexane, -40 deg C, 80 min 5: acetic acid / 3 h / Ambient temperature View Scheme

pent-1-yn-5-ol (5390-04-5) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1) LiNH2 / 1) NH3(l), 3 h; 2) abs THF, 20-25 deg C, 13 h. 2: 80 percent / nickel acetate, NaBH4, ethylene diamine / ethanol 3: 80 percent / pyridinium chlorochromate / CH2Cl2 4: 1) butyllithium, 2) butyllithium, 3) ethanol / 1) abs. THF, hexan, -30 deg C, 90 min; 2) abs. THF, hexan, 40 min at -60 deg C and 15 min at -30 deg C; 3) 30 min at -30 deg C and 24 h at -40 deg C. 5: 92 percent / glacial acetic acid / Heating View Scheme
Multi-step reaction with 5 steps 1: 76 percent / LiNH2, NH3 (liquid) / tetrahydrofuran / 5 h 2: ethylene diamine, H2 / Ni(OAc)2.4H2O, NaBH4 / ethanol; H2O 3: 90 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 4: 1.) n-BuLi / 1.) ether, hexane, RT, 1 h; 2.) ether, hexane, -40 deg C, 80 min 5: acetic acid / 3 h / Ambient temperature View Scheme
Multi-step reaction with 6 steps 1: 81 percent / LiNH2, NH3 (liquid) / 4 h 2: H2, Na/NH3 / Ni(OAc)2.4H2O, NaBH4 3: 81 percent / triphenylphosphine, Br2, pyridine / CH2Cl2; CCl4 / Ambient temperature 4: acetonitrile / Heating 5: 1.) 2M dimsyl sodium / 1.) THF, DMSO, RT, 30 min; 2.) THF, DMSO, a.) -30 deg C up to RT, RT 6: acetic acid View Scheme

(Z)-11-(2'-tetrahydropyranyloxy)undec-4-en-1-ol (94141-78-3) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / pyridinium chlorochromate / CH2Cl2 2: 1) butyllithium, 2) butyllithium, 3) ethanol / 1) abs. THF, hexan, -30 deg C, 90 min; 2) abs. THF, hexan, 40 min at -60 deg C and 15 min at -30 deg C; 3) 30 min at -30 deg C and 24 h at -40 deg C. 3: 92 percent / glacial acetic acid / Heating View Scheme
Multi-step reaction with 3 steps 1: 90 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 2: 1.) n-BuLi / 1.) ether, hexane, RT, 1 h; 2.) ether, hexane, -40 deg C, 80 min 3: acetic acid / 3 h / Ambient temperature View Scheme

11-<(tetrahydro-2H-pyran-2-yl)oxy>undec-4-yn-1-ol (94141-77-2) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / nickel acetate, NaBH4, ethylene diamine / ethanol 2: 80 percent / pyridinium chlorochromate / CH2Cl2 3: 1) butyllithium, 2) butyllithium, 3) ethanol / 1) abs. THF, hexan, -30 deg C, 90 min; 2) abs. THF, hexan, 40 min at -60 deg C and 15 min at -30 deg C; 3) 30 min at -30 deg C and 24 h at -40 deg C. 4: 92 percent / glacial acetic acid / Heating View Scheme
Multi-step reaction with 6 steps 1: 78 percent / pyridinium fluorochromate / CH2Cl2 / 3 h / Ambient temperature 2: 1) NaNH2 / 1) THF, HMPA, r.t., 90 min, 2) THF, r.t., 6 h 3: 90 percent / PPTS, pyridine / methanol / 2 h / Heating 4: pyridine / DMAP / 2 h / Ambient temperature 5: 1.33 g / aq.NaNO2, 6M HNO3 / 0.5 h / 70 - 75 °C 6: 94 percent / H2, quinoline / Lindlar catalyst / ethanol / 760 Torr View Scheme
Multi-step reaction with 4 steps 1: ethylene diamine, H2 / Ni(OAc)2.4H2O, NaBH4 / ethanol; H2O 2: 90 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 3: 1.) n-BuLi / 1.) ether, hexane, RT, 1 h; 2.) ether, hexane, -40 deg C, 80 min 4: acetic acid / 3 h / Ambient temperature View Scheme

(Z)-11-(2'-tetrahydropyranyloxy)undec-4-en-1-al (94141-79-4) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) butyllithium, 2) butyllithium, 3) ethanol / 1) abs. THF, hexan, -30 deg C, 90 min; 2) abs. THF, hexan, 40 min at -60 deg C and 15 min at -30 deg C; 3) 30 min at -30 deg C and 24 h at -40 deg C. 2: 92 percent / glacial acetic acid / Heating View Scheme
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) ether, hexane, RT, 1 h; 2.) ether, hexane, -40 deg C, 80 min 2: acetic acid / 3 h / Ambient temperature View Scheme

(E)-4-none-1-ol (16695-34-4) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 82 percent / PCC / CHCl3 / 2 h 2: 1.) PPh3, t-BuOK / 1.) 160 deg C, 8 h; THF, -30 deg C, 0.5 h, 2.) -70 deg C, 3 h; room temperature, overnight 3: 81 percent / acetic acid / 5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 65 percent / pyridine, phosphorus tribromide / benzene / 6 h / Heating 2: tetrahydrofuran / Ambient temperature 3: 1.) sodium hexamethyldisilazylamide / 1.) THF, RT, 1 h, 2.) THF, from -60 to -50 deg C, 6 h View Scheme
Multi-step reaction with 4 steps 1: 81 percent / triphenylphosphine, Br2, pyridine / CH2Cl2; CCl4 / Ambient temperature 2: acetonitrile / Heating 3: 1.) 2M dimsyl sodium / 1.) THF, DMSO, RT, 30 min; 2.) THF, DMSO, a.) -30 deg C up to RT, RT 4: acetic acid View Scheme
Multi-step reaction with 5 steps 1: (i) TsCl, Py, (ii) LiBr, DMF 2: Heating 3: dimsyl sodium / dimethylsulfoxide 4: LiAlH4 / diethyl ether 5: Py View Scheme

1-hepten-3-ol (4938-52-7) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 77 percent / propionic acid / 2 h / 135 - 137 °C 2: 78 percent / LiAlH4 / diethyl ether / 0 - 20 °C 3: 82 percent / PCC / CHCl3 / 2 h 4: 1.) PPh3, t-BuOK / 1.) 160 deg C, 8 h; THF, -30 deg C, 0.5 h, 2.) -70 deg C, 3 h; room temperature, overnight 5: 81 percent / acetic acid / 5 h / Heating View Scheme
Multi-step reaction with 7 steps 1: propionic acid / 145 °C 2: LiAlH4 / diethyl ether 3: (i) TsCl, Py, (ii) LiBr, DMF 4: Heating 5: dimsyl sodium / dimethylsulfoxide 6: LiAlH4 / diethyl ether 7: Py View Scheme

(E)-non-4-enal (2277-16-9) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) PPh3, t-BuOK / 1.) 160 deg C, 8 h; THF, -30 deg C, 0.5 h, 2.) -70 deg C, 3 h; room temperature, overnight 2: 81 percent / acetic acid / 5 h / Heating View Scheme

ethyl (4E)-non-4-enoate (69361-38-2) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 78 percent / LiAlH4 / diethyl ether / 0 - 20 °C 2: 82 percent / PCC / CHCl3 / 2 h 3: 1.) PPh3, t-BuOK / 1.) 160 deg C, 8 h; THF, -30 deg C, 0.5 h, 2.) -70 deg C, 3 h; room temperature, overnight 4: 81 percent / acetic acid / 5 h / Heating View Scheme
Multi-step reaction with 6 steps 1: LiAlH4 / diethyl ether 2: (i) TsCl, Py, (ii) LiBr, DMF 3: Heating 4: dimsyl sodium / dimethylsulfoxide 5: LiAlH4 / diethyl ether 6: Py View Scheme

1,7-heptandiol (629-30-1) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / pyridine / benzene / 6 h 2: 75 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1.5 h 3: 1.) sodium hexamethyldisilazylamide / 1.) THF, RT, 1 h, 2.) THF, from -60 to -50 deg C, 6 h View Scheme

1,2-dibromohexane (624-20-4) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions

Yield

Multi-step reaction with 7 steps 1: 85 percent / potassium hydroxide, tetrabutylammonium chloride, 2,5-hexanediol / 0.5 h 2: 1.) lithium amide, liq. ammonia / 1.) THF, 1 h, 2.) THF, 2 h 3: p-toluenesulfonic acid / methanol / 24 h 4: 80 percent / LiAlH4, / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 2 h / Heating 5: 65 percent / pyridine, phosphorus tribromide / benzene / 6 h / Heating 6: tetrahydrofuran / Ambient temperature 7: 1.) sodium hexamethyldisilazylamide / 1.) THF, RT, 1 h, 2.) THF, from -60 to -50 deg C, 6 h View Scheme

(E)-4-nonen-1-yl bromide (16695-35-5) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / Ambient temperature 2: 1.) sodium hexamethyldisilazylamide / 1.) THF, RT, 1 h, 2.) THF, from -60 to -50 deg C, 6 h View Scheme
Multi-step reaction with 3 steps 1: acetonitrile / Heating 2: 1.) 2M dimsyl sodium / 1.) THF, DMSO, RT, 30 min; 2.) THF, DMSO, a.) -30 deg C up to RT, RT 3: acetic acid View Scheme
Multi-step reaction with 4 steps 1: Heating 2: dimsyl sodium / dimethylsulfoxide 3: LiAlH4 / diethyl ether 4: Py View Scheme

4-nonyne-1-ol (49826-98-4) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / LiAlH4, / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 2 h / Heating 2: 65 percent / pyridine, phosphorus tribromide / benzene / 6 h / Heating 3: tetrahydrofuran / Ambient temperature 4: 1.) sodium hexamethyldisilazylamide / 1.) THF, RT, 1 h, 2.) THF, from -60 to -50 deg C, 6 h View Scheme
Multi-step reaction with 5 steps 1: H2, Na/NH3 / Ni(OAc)2.4H2O, NaBH4 2: 81 percent / triphenylphosphine, Br2, pyridine / CH2Cl2; CCl4 / Ambient temperature 3: acetonitrile / Heating 4: 1.) 2M dimsyl sodium / 1.) THF, DMSO, RT, 30 min; 2.) THF, DMSO, a.) -30 deg C up to RT, RT 5: acetic acid View Scheme

acetic acid 7-hydroxyheptyl ester (59694-63-2) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1.5 h 2: 1.) sodium hexamethyldisilazylamide / 1.) THF, RT, 1 h, 2.) THF, from -60 to -50 deg C, 6 h View Scheme

hex-1-yne (693-02-7) + monobromohexylene → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions

Yield

Multi-step reaction with 6 steps 1: 1.) lithium amide, liq. ammonia / 1.) THF, 1 h, 2.) THF, 2 h 2: p-toluenesulfonic acid / methanol / 24 h 3: 80 percent / LiAlH4, / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 2 h / Heating 4: 65 percent / pyridine, phosphorus tribromide / benzene / 6 h / Heating 5: tetrahydrofuran / Ambient temperature 6: 1.) sodium hexamethyldisilazylamide / 1.) THF, RT, 1 h, 2.) THF, from -60 to -50 deg C, 6 h View Scheme

2-Non-4-ynyloxy-tetrahydro-pyran (65370-57-2) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: p-toluenesulfonic acid / methanol / 24 h 2: 80 percent / LiAlH4, / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 2 h / Heating 3: 65 percent / pyridine, phosphorus tribromide / benzene / 6 h / Heating 4: tetrahydrofuran / Ambient temperature 5: 1.) sodium hexamethyldisilazylamide / 1.) THF, RT, 1 h, 2.) THF, from -60 to -50 deg C, 6 h View Scheme

2-(5-bromopentyloxy)tetrahydropyran (37935-47-0) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Mg; 2.) Li2CuCl4 / 1.) THF; 2.) 5 h, -10 deg C; 2: 80 percent / acetic acid, pyridine / 12 h / Ambient temperature View Scheme

(E)-oct-3-en-1-ol (18185-81-4, 20125-84-2, 20125-85-3) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 7 steps 1: 68 percent / PBr3, pyridine / diethyl ether / 2 h / Heating 2: 1.) ethylmagnesiumbromide, 2.) cuprous chloride / 1.) THF, 6 h, 40-50 deg C 3: 58 percent / PTS / methanol / 6 h / 55 °C 4: H2, quinoline / Lindlar's catalyst / hexane 5: PBr3, pyridine / diethyl ether 6: 1.) Mg; 2.) Li2CuCl4 / 1.) THF; 2.) 5 h, -10 deg C; 7: 80 percent / acetic acid, pyridine / 12 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: 83 percent / Br2, triphenylphosphine / CCl4 / 1 h / Ambient temperature 2: 1.) Li, ferric chloride, liquid ammonia / 1.) THF, 1 h, 2.) DMSO, -35 deg C, 3 h 3: TsOH, H2O / methanol / 24 h / Ambient temperature 4: NaBH4, ethylenediamine, nickel acetate / ethanol / Ambient temperature 5: pyridine / 24 h / Ambient temperature View Scheme

(E)-oct-3-enoic acid (5163-67-7) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 9 steps 1: 69 percent / triethylamine / CH2Cl2 / 4 h / 0 °C 2: 68 percent / NaBH4 / ethanol / 3 h 3: 68 percent / PBr3, pyridine / diethyl ether / 2 h / Heating 4: 1.) ethylmagnesiumbromide, 2.) cuprous chloride / 1.) THF, 6 h, 40-50 deg C 5: 58 percent / PTS / methanol / 6 h / 55 °C 6: H2, quinoline / Lindlar's catalyst / hexane 7: PBr3, pyridine / diethyl ether 8: 1.) Mg; 2.) Li2CuCl4 / 1.) THF; 2.) 5 h, -10 deg C; 9: 80 percent / acetic acid, pyridine / 12 h / Ambient temperature View Scheme
Multi-step reaction with 7 steps 1: 89 percent / TsOH / 24 h / Ambient temperature 2: 93 percent / diisobutylaluminum hydride (DIBAH) / diethyl ether; toluene / 2 h / -20 °C 3: 83 percent / Br2, triphenylphosphine / CCl4 / 1 h / Ambient temperature 4: 1.) Li, ferric chloride, liquid ammonia / 1.) THF, 1 h, 2.) DMSO, -35 deg C, 3 h 5: TsOH, H2O / methanol / 24 h / Ambient temperature 6: NaBH4, ethylenediamine, nickel acetate / ethanol / Ambient temperature 7: pyridine / 24 h / Ambient temperature View Scheme

(E)-1-oct-3-enyl bromide (53155-10-5) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) ethylmagnesiumbromide, 2.) cuprous chloride / 1.) THF, 6 h, 40-50 deg C 2: 58 percent / PTS / methanol / 6 h / 55 °C 3: H2, quinoline / Lindlar's catalyst / hexane 4: PBr3, pyridine / diethyl ether 5: 1.) Mg; 2.) Li2CuCl4 / 1.) THF; 2.) 5 h, -10 deg C; 6: 80 percent / acetic acid, pyridine / 12 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 1.) Li, ferric chloride, liquid ammonia / 1.) THF, 1 h, 2.) DMSO, -35 deg C, 3 h 2: TsOH, H2O / methanol / 24 h / Ambient temperature 3: NaBH4, ethylenediamine, nickel acetate / ethanol / Ambient temperature 4: pyridine / 24 h / Ambient temperature View Scheme

C11H18O4 (126629-19-4) → 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8)

Conditions

Yield

Multi-step reaction with 8 steps 1: 68 percent / NaBH4 / ethanol / 3 h 2: 68 percent / PBr3, pyridine / diethyl ether / 2 h / Heating 3: 1.) ethylmagnesiumbromide, 2.) cuprous chloride / 1.) THF, 6 h, 40-50 deg C 4: 58 percent / PTS / methanol / 6 h / 55 °C 5: H2, quinoline / Lindlar's catalyst / hexane 6: PBr3, pyridine / diethyl ether 7: 1.) Mg; 2.) Li2CuCl4 / 1.) THF; 2.) 5 h, -10 deg C; 8: 80 percent / acetic acid, pyridine / 12 h / Ambient temperature View Scheme

Dimethyldisulphide (624-92-0) + 1-acetoxyhexadeca-7Z,11E-diene (53042-79-8) → 2-<1-acetoxy-7-(methylthio)heptan-7-yl>-5-<1-(methylthio)pentan-1-yl>tetrahydrothiophene (105836-08-6)

Conditions	Yield
With iodine at 50℃; for 5h;	80%

1-acetoxyhexadeca-7Z,11E-diene (53042-79-8) → (7Z,11E)-hexadeca-7,11-dien-1-ol (53963-09-0)

Conditions	Yield
With potassium carbonate In methanol

1-acetoxyhexadeca-7Z,11E-diene (53042-79-8) → (7Z,11E)-7,11-hexadecadienal

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / methanol 2: pyridinium chlorochromate / CH2Cl2 View Scheme

Upstream product

• 629-11-8 1,6-hexanediol 
• 22054-13-3 7-hydroxyheptanal 
• 69361-44-0 (5E)-5-decen-1-ynyltrimethylsilane 
• 29425-54-5 acetic acid 7-oxo-heptyl ester 
• 59499-33-1 (7Z,11E)-7,11-Hexadecadiensaeure-ethylester 
• 3990-05-4 ethyl 6-formylhexanoate 
• 59512-90-2 <(E)-4-Nonenyl>-triphenylphosphonium-bromid 
• 4286-55-9 1-bromo-6-hexanol 
• 97-99-4 Tetrahydrofurfuryl alcohol 
• 122554-99-8 11-<(tetrahydro-2H-pyran-2-yl)oxy>undec-4-yn-1-al 
• 122555-00-4 (Z)-hexadec-7-yn-11-en-1-ol 
• 53042-80-1 (Z)-hexadec-7-yn-11-enyl-1-acetate 
• 53155-13-8 (Z)-1-<(tetrahydro-2H-pyran-2-yl)oxy>hexadec-7-yn-11-ene 
• 3003-84-7 Tetrahydrofurfuryl chloride 

Downstream Products

• 53963-09-0 (7Z,11E)-hexadeca-7,11-dien-1-ol 

Relevant articles and documents

Insect pheromones and their analogs. LVIII. Synthesis of hexadeca-7Z,11E-dien-1-yl acetate - A component of the sex pheromones of Pectinophora gossypiella and Sitotroga cerealella

A new synthesis of hexadeca-7Z,11E-dien-1-yl acetate - a component of the sex pheromones of the pink bollworm (Pectinophora gossypiella) and the Angoumois grain moth (Sitotroga cerealella) - is proposed that is based on a thermal Claisen rearrangement. Scientific-Research Institute of Small-Tonnage Chemical Products and Reagents, Ufa, fax 8-(3472) 43 17 31.

STEREOSPECIFIC SYNTHESIS OF COMPONENTS OF THE NATURAL SEX PHEROMONE OF Pectinophora gossypiella

A multistage stereospecific synthesis of components of the natural pheromone was realized.Conditions were found for stereospecific trans-reduction of the triple bonds.A procedure was developed for regiospecific dehydrohalogenation of 1,2-dibromoalkanes.Conditions giving the Z and E isomers in ratio of 96 : 4 were found for the Wittig reaction.

PHEROMONES OF INSECTS AND THEIR ANALOGS XXXIII. SYNTHESIS OF HEXADEC-7Z,11E-DIEN-1-YL ACETATE - THE SEX PHEROMONE OF Sitotroga cerealella AND A COMPONENT OF THE SEX PHEROMONE OF Pectinophora gossypiella

From cyclohexene and caproaldehyde, using ozonolysis and the Knoevenagel reaction, we have synthesized hexadeca-7Z,11E-dien-1-yl acetate - the sex pheromone of Sitotroga cerealella and a component of the sex pheromone of Pectinophora gossypiella.

SYNTHETIC INVESTIGATIONS IN THE FIELD OF INSECT ATTRACTANTS (SEX ATTRACTANTS). X. SYNTHESIS OF THE ACETATES OF CIS-7,CIS-11- AND CIS-7,TRANS-11-HEXADECADIEN-1-OL, THE SEX PHEROMONES OF THE PINK BOLLWORM MOTH Pectinophora gossypiella S. (LEPIDOPTERA, GELECHIIDAE) AND THE GRAIN MOTH Sit...

The synthesis of the acetates of cis-7,cis-11- and cis-7,trans-11-hexadecadien-1-ol, which are the sex pheromones of the pink bollworm moth Pectinophora gossypiella and the Angoumois grain moth Sitotroga cerealella, and their geometric isomers on the basis of the Wittig reaction and of the unsaturated functionally ω-substituted aldehydes is described.The alkylation of the dilithium derivative of 4-pentyn-1-ol by 2-(6-bromohexyloxy)tetrahydropyran in a mixture of liquid ammonia and THF gave a 40percent yield of 11-(2-tetrahydropyranyloxy)-4-undecyn-1-ol, which was hydrogenated selectively to 11-(2-tetrahydropyranyloxy)-cis-4-undecen-1-ol or was reduced to 11-(2-tetrahydropyranyloxy)-trans-4-undecen-1-ol.Both alcohols were oxidized by pyridinium chlorochromate to 11-(2-tetrahydropyranyloxy)-cis-4-undecenal and 11-(2-tetrahydropyranyloxy)-trans-4-undecenal.The reaction of both aldehydes with amyltriphenylphosphonium bromide under stereocontrolled conditions followed by acetolysis gave the acetates of cis-7,cis-11-, cis-7,trans-11-, trans-7,cis-11-, and trans-7,trans-11-hexadecadien-1-ols and a mixture of the acetates of cis-7,cis-11- and cis-7,trans-11-hexadecadien-1-ol (gossyplure).

A Practical Synthesis of Sex Pheromones of Pink Bollworm: Gossyplure

The practical synthesis of (Z,Z) and (Z,E)-7,11-hexadecadienyl acetates, sex pheromones of pink bollworm (gossyplure) is described.

STEREOSELECTIVE AND VERSATILE APPROACH FOR THE SYNTHESIS OF GOSSYPLURE AND ITS COMPONENTS

Efficient synthetic routes to gossyplure and its components (1a and 1b) were formulated.The three key units viz the alkynol 3, the bromide 5, and the alkanal 13 were derived from easily accessible starting materials.Alkylation of 3 with 5, and subsequent semihydrogenation followed by oxidation, provided the C11-alkenal 8 which was subjected to a stereocontrolled Wittig reaction with a C5-phosphonium salt, to yield directly the disired pheromone (1a + 1b).The synthesis of its individual components involved the manipulation via an acetylenic intermediate, viz the alkynol 14 which was obtained through alkylation of 3.A sequence of well-established reactions on 14, then provided the corresponding (E)- and (Z)-alkenylphosphonium salts which upon a (Z)-specific Wittig olefination with the C7-aldehyde (13), led to the stereoselective synthesis of 1a and 1b.

THE STEREOSELECTIVE α-ALKYLATION OF CHIRAL β-HYDROXY ESTERS AND SOME APPLICATIONS THEREOF

The stereoselectivity of the α-alkylation of chiral β-hydroxy ester is discussed.The configuration of the alkylated product was proved chemically (Scheme 2) .A one pot aldol-alkylation reaction was developed leading stereoselectively to racemic(S*,S*)-α-alkyl-β-hydroxy ester (Scheme 3,4) .Baker's yeast reduction of 2-alkyl-3-keto ester led to valuable chiral (2RS,3S)-intermediates, which were converted via the corresponding dianion to compounds with a chiral quaternary C atom (Scheme 6) .Synthetic applications of the above findings are shown in the synthesis of various chiral compounds (Scheme 8 and 9) .