JP4347735B2 - 新規な脂肪族ハロゲン化合物及びその製造方法 - Google Patents
新規な脂肪族ハロゲン化合物及びその製造方法 Download PDFInfo
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- JP4347735B2 JP4347735B2 JP2004090871A JP2004090871A JP4347735B2 JP 4347735 B2 JP4347735 B2 JP 4347735B2 JP 2004090871 A JP2004090871 A JP 2004090871A JP 2004090871 A JP2004090871 A JP 2004090871A JP 4347735 B2 JP4347735 B2 JP 4347735B2
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- Prior art keywords
- methyl
- dodecyl
- reaction
- chloride
- acetate
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- -1 aliphatic halogen compound Chemical class 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- KSTCXBJXIXYMTG-UHFFFAOYSA-N 1-chloro-10-methyldodecane Chemical compound CCC(C)CCCCCCCCCCl KSTCXBJXIXYMTG-UHFFFAOYSA-N 0.000 claims description 19
- WUVOJIMYHUYERX-UHFFFAOYSA-N 10-methyldodecyl acetate Chemical compound CCC(C)CCCCCCCCCOC(C)=O WUVOJIMYHUYERX-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- JTYUIAOHIYZBPB-UHFFFAOYSA-N 1-bromo-6-chlorohexane Chemical compound ClCCCCCCBr JTYUIAOHIYZBPB-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000007818 Grignard reagent Substances 0.000 description 11
- 150000004795 grignard reagents Chemical class 0.000 description 11
- 239000002904 solvent Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000004891 communication Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 241001122767 Theaceae Species 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 239000000877 Sex Attractant Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 3
- HKKQSNCJIFHCQD-UHFFFAOYSA-N 1-chloro-4-methylhexane Chemical compound CCC(C)CCCCl HKKQSNCJIFHCQD-UHFFFAOYSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- FQOCWCFPCYMAJQ-UHFFFAOYSA-N 1-bromo-10-methyldodecane Chemical compound BrCCCCCCCCCC(CC)C FQOCWCFPCYMAJQ-UHFFFAOYSA-N 0.000 description 2
- GRAPINPHMVWPKL-UHFFFAOYSA-N 3,10-dimethyldodecane Chemical group CCC(C)CCCCCCC(C)CC GRAPINPHMVWPKL-UHFFFAOYSA-N 0.000 description 2
- PYSBBBMFXRFUNP-UHFFFAOYSA-N 3,16-dimethyloctadecane Chemical compound CCC(C)CCCCCCCCCCCCC(C)CC PYSBBBMFXRFUNP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000005667 attractant Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000031902 chemoattractant activity Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000009815 homocoupling reaction Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YJINQJFQLQIYHX-PLNGDYQASA-N 11Z-Tetradecenyl acetate Chemical group CC\C=C/CCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-PLNGDYQASA-N 0.000 description 1
- YMOHUOSDPGVWND-UHFFFAOYSA-N 2-chlorotridecane Chemical compound CCCCCCCCCCCC(C)Cl YMOHUOSDPGVWND-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001672674 Adoxophyes honmai Species 0.000 description 1
- HMMLQEJHLSSOBP-UHFFFAOYSA-N CC(CCCCCCCCCCl)CC.CC(CCCCCCCCCCl)CC Chemical compound CC(CCCCCCCCCCl)CC.CC(CCCCCCCCCCl)CC HMMLQEJHLSSOBP-UHFFFAOYSA-N 0.000 description 1
- PCSQNQGGDIHLJP-UHFFFAOYSA-M CCC(C)CCC[Mg]Cl Chemical compound CCC(C)CCC[Mg]Cl PCSQNQGGDIHLJP-UHFFFAOYSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241001012098 Omiodes indicata Species 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OPHUWKNKFYBPDR-UHFFFAOYSA-N copper lithium Chemical compound [Li].[Cu] OPHUWKNKFYBPDR-UHFFFAOYSA-N 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- FYYHWMGAXLPEAU-OUBTZVSYSA-N magnesium-25 atom Chemical compound [25Mg] FYYHWMGAXLPEAU-OUBTZVSYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Agric.Biol.Chem.,46,1925(1982) J.Chem.Ecol.,8,41(1982)
〔4−メチル−ヘキシルマグネシウムクロリドの合成〕
反応器にテトラヒドロフラン100g、金属マグネシウム25g(1.03モル)、ヨウ素片0.2gを加え、窒素雰囲気下、65〜70℃で少量の4−メチルヘキシルクロリドを加えて反応を開始させた。
〔10−メチル−ドデシルクロリドの合成〕
反応器に窒素雰囲気下、テトラヒドロフラン100g、ヨウ化第1銅2g、1−ブロモ−6−クロロヘキサン195.5g(0.98モル)を加え、0℃に冷却して、そこへ上記グリニャール試薬4−メチル−ヘキシルマグネシウムクロリドのテトラヒドロフラン溶液を20〜40℃で冷却しながら滴下した。滴下終了後、20℃で1時間攪拌した。
41(52),43(52),56(59),57(100),71(35),85(24),98(16),105(5),119(10),133(15),147(6),189(39),203(1),218(3),220(1)
〔赤外吸収スペクトル(単位cm−1)〕
2958(-CH3),2925(-CH2-),2854,1463,1377,1309,1290,723,655,532
〔1H−核磁気共鳴スペクトル(300MHz,CDCl3;単位ppm)〕
0.831-0.879(6H,-CH3),1.036-1.475(m,17H),1.717-1.812(m,2H),3.497-3.542(t,2H)
〔13C−核磁気共鳴スペクトル(300MHz,CDCl3;単位ppm)〕
11.378,19.187,26.905,27.096,28.921,29.493,29.499,29.608,29.982,32.684,36.639,45.059
〔10−メチル−ドデシルアセタート(チャノコカクモンハマキの性フェロモン成分)の合成〕
反応器に10−メチル−ドデシルクロリド188g(0.86モル)と無水酢酸カリウム170g(1.7モル)、酢酸150gを仕込み、窒素雰囲気下180℃で8時間攪拌した。反応後、減圧下で酢酸を約100g回収した後、純水300gで水和し、5重量%重曹水400mlで2回洗浄して減圧蒸留したところ、10−メチル−ドデシルアセタート193g(0.80モル;収率92%)が得られた。得られた物質の沸点は、115〜120℃/3mmHgであり、4−メチル−ヘキシルクロリドからの全収率は、80.0%であった。
〔10−メチル−ドデシルブロミドの合成〕
1−ブロモ−6−クロロヘキサン195.5gの代わりに1,6−ジブロモヘキサン244g(1.0モル)を用いる以外は、実施例と同様に行ったところ、10−メチル−ドデシルブロミド168g(0.64モル;収率64%)が得られた。このとき副成した3,16−ジメチル−オクタデカンは約51gであった。
Claims (2)
- 4−メチル−ヘキシルマグネシウムハライドと1−ブロモ−6−クロロヘキサンとを、銅触媒の存在下、反応させることを特徴とする10−メチル−ドデシルクロリドの製造方法。
- 請求項1に記載の方法で製造された10−メチル−ドデシルクロリドと酢酸アルカリ金属塩とを反応させることを特徴とする10−メチル−ドデシルアセタートの製造方法。
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JP2004090871A JP4347735B2 (ja) | 2004-03-26 | 2004-03-26 | 新規な脂肪族ハロゲン化合物及びその製造方法 |
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JP2004090871A JP4347735B2 (ja) | 2004-03-26 | 2004-03-26 | 新規な脂肪族ハロゲン化合物及びその製造方法 |
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JP4347735B2 true JP4347735B2 (ja) | 2009-10-21 |
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KR101547843B1 (ko) | 2013-11-11 | 2015-08-27 | 경상대학교산학협력단 | 신규한 알킬 할라이드 화합물 및 이의 제조방법 |
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