JPH0158169B2 - - Google Patents
Info
- Publication number
- JPH0158169B2 JPH0158169B2 JP12342484A JP12342484A JPH0158169B2 JP H0158169 B2 JPH0158169 B2 JP H0158169B2 JP 12342484 A JP12342484 A JP 12342484A JP 12342484 A JP12342484 A JP 12342484A JP H0158169 B2 JPH0158169 B2 JP H0158169B2
- Authority
- JP
- Japan
- Prior art keywords
- terpene
- formula
- chloride
- tetramethylene
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 terpene ketone Chemical class 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 235000007586 terpenes Nutrition 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- RBGLEUBCAJNCTR-UHFFFAOYSA-N 6,10-dimethylundecan-2-one Chemical compound CC(C)CCCC(C)CCCC(C)=O RBGLEUBCAJNCTR-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- LSEHYGOQRNHJHH-UHFFFAOYSA-M [Mg]CCCC[Mg]Cl Chemical compound [Mg]CCCC[Mg]Cl LSEHYGOQRNHJHH-UHFFFAOYSA-M 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 6
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 5
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- HNZUNIKWNYHEJJ-FMIVXFBMSA-N geranyl acetone Chemical compound CC(C)=CCC\C(C)=C\CCC(C)=O HNZUNIKWNYHEJJ-FMIVXFBMSA-N 0.000 description 2
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229940032094 squalane Drugs 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 1
- OBTJQIDKRSRPHY-UHFFFAOYSA-N 2,6,10,15,19,23-hexamethyltetracosane-10,15-diol Chemical compound CC(C)CCCC(C)CCCC(C)(O)CCCCC(C)(O)CCCC(C)CCCC(C)C OBTJQIDKRSRPHY-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005575 aldol reaction Methods 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12342484A JPS611631A (ja) | 1984-06-14 | 1984-06-14 | テルペンジオ−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12342484A JPS611631A (ja) | 1984-06-14 | 1984-06-14 | テルペンジオ−ルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS611631A JPS611631A (ja) | 1986-01-07 |
| JPH0158169B2 true JPH0158169B2 (fr) | 1989-12-11 |
Family
ID=14860212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12342484A Granted JPS611631A (ja) | 1984-06-14 | 1984-06-14 | テルペンジオ−ルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS611631A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03200075A (ja) * | 1989-12-28 | 1991-09-02 | Ngk Insulators Ltd | 導通状態試験装置 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101891579B (zh) * | 2010-06-21 | 2013-06-19 | 上虞新和成生物化工有限公司 | 一种角鲨烯的合成方法 |
-
1984
- 1984-06-14 JP JP12342484A patent/JPS611631A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03200075A (ja) * | 1989-12-28 | 1991-09-02 | Ngk Insulators Ltd | 導通状態試験装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS611631A (ja) | 1986-01-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS58159432A (ja) | 分枝二量化アルコ−ルの製造方法 | |
| JPH0456816B2 (fr) | ||
| JPH01132543A (ja) | アルファ‐イソホロンからベータ‐イソホロンを製造する方法 | |
| JPH0158169B2 (fr) | ||
| JPS62129236A (ja) | メチルイソプロピルケトン及びジエチルケトンの製法 | |
| JP2003171335A (ja) | 大環状ケトン化合物の製造方法 | |
| JP3386596B2 (ja) | ５（ｅ），８（ｚ），１１（ｚ）−テトラデカトリエン−２−オンの製造方法 | |
| JPS6217576B2 (fr) | ||
| JPS5855129B2 (ja) | ２−置換または無置換のゲラニル酢酸エステル類の製造方法 | |
| JPH0475224B2 (fr) | ||
| Menicagli et al. | Triisobutylaluminum assisted reductive rearrangement of 2-ethoxy-4-alkyl-2, 3-dihydrofurans | |
| JPS5838242A (ja) | Ｎ−置換メタクリルアミド及びアクリルアミドの製造方法 | |
| JPH0537140B2 (fr) | ||
| JPH0466216B2 (fr) | ||
| JP2697198B2 (ja) | ２―ヒドロキシ―３，３，３―トリフルオロプロピオニトリルの製造方法 | |
| JPH0146A (ja) | ４−ヒドロキシ−２−シクロペンテノン誘導体の製造法 | |
| JPS6013036B2 (ja) | エチニルマグネシウムクロリドの製造法 | |
| JPS63295562A (ja) | ４−メチルイミダゾールの製法 | |
| JP4288372B2 (ja) | アルファーピロン類およびその製造方法 | |
| JP2691760B2 (ja) | α―（３―ベンジルフェニル）プロピオン酸誘導体の製造方法 | |
| JP3878701B2 (ja) | ４−ヒドロキシ−１−アルキン類の製造法 | |
| JP2542503B2 (ja) | シクロヘキサノン誘導体の合成法 | |
| JP4641772B2 (ja) | フラノンの製造方法 | |
| Zakharkin et al. | Simple synthesis of 15-hydroxypentadecanoic acid from l0-undecenoic acid | |
| JPH0535134B2 (fr) |