JPS59225176A - リナロ−ルオキサイドの製造法 - Google Patents
リナロ−ルオキサイドの製造法Info
- Publication number
- JPS59225176A JPS59225176A JP10017683A JP10017683A JPS59225176A JP S59225176 A JPS59225176 A JP S59225176A JP 10017683 A JP10017683 A JP 10017683A JP 10017683 A JP10017683 A JP 10017683A JP S59225176 A JPS59225176 A JP S59225176A
- Authority
- JP
- Japan
- Prior art keywords
- type
- linalool
- reaction
- pyran
- furan
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- BRHDDEIRQPDPMG-UHFFFAOYSA-N Linalyl oxide Chemical compound CC(C)(O)C1CCC(C)(C=C)O1 BRHDDEIRQPDPMG-UHFFFAOYSA-N 0.000 title abstract description 19
- 239000001278 2-(5-ethenyl-5-methyloxolan-2-yl)propan-2-ol Substances 0.000 title abstract description 18
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims abstract description 10
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims abstract description 10
- 229930007744 linalool Natural products 0.000 claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 3
- 239000011707 mineral Substances 0.000 claims abstract description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 230000000640 hydroxylating effect Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 239000003292 glue Substances 0.000 claims 1
- 150000004965 peroxy acids Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 238000013329 compounding Methods 0.000 abstract description 2
- 230000018044 dehydration Effects 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- 238000005805 hydroxylation reaction Methods 0.000 abstract 4
- 230000033444 hydroxylation Effects 0.000 abstract 2
- 238000007363 ring formation reaction Methods 0.000 abstract 2
- 239000010648 geranium oil Substances 0.000 abstract 1
- 235000019717 geranium oil Nutrition 0.000 abstract 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 abstract 1
- 239000012438 synthetic essential oil Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- GPVKUNYYWAKDRY-UHFFFAOYSA-N Linalooloxid Natural products CC(C)C1CCC(C)(C=C)O1 GPVKUNYYWAKDRY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- -1 vinyl-5-hydroxy-tetrahydropyran Chemical compound 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10017683A JPS59225176A (ja) | 1983-06-07 | 1983-06-07 | リナロ−ルオキサイドの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10017683A JPS59225176A (ja) | 1983-06-07 | 1983-06-07 | リナロ−ルオキサイドの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59225176A true JPS59225176A (ja) | 1984-12-18 |
| JPH0370704B2 JPH0370704B2 (enrdf_load_stackoverflow) | 1991-11-08 |
Family
ID=14267003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10017683A Granted JPS59225176A (ja) | 1983-06-07 | 1983-06-07 | リナロ−ルオキサイドの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59225176A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6703218B2 (en) | 2000-11-07 | 2004-03-09 | Haarman & Reimer Gmbh | Process for the preparation of linalool oxide or of linalool oxide-containing mixtures |
| CN105801529A (zh) * | 2016-05-22 | 2016-07-27 | 上海应用技术学院 | 一种碳酸芳樟醇氧化物（吡喃型和呋喃型）酯乙酯的制备方法 |
-
1983
- 1983-06-07 JP JP10017683A patent/JPS59225176A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| LIEBIGS ANNALEN DER CHEMIE=1964 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6703218B2 (en) | 2000-11-07 | 2004-03-09 | Haarman & Reimer Gmbh | Process for the preparation of linalool oxide or of linalool oxide-containing mixtures |
| CN105801529A (zh) * | 2016-05-22 | 2016-07-27 | 上海应用技术学院 | 一种碳酸芳樟醇氧化物（吡喃型和呋喃型）酯乙酯的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0370704B2 (enrdf_load_stackoverflow) | 1991-11-08 |
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