JPS562978A - Preparation of 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran - Google Patents
Preparation of 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyranInfo
- Publication number
- JPS562978A JPS562978A JP7860279A JP7860279A JPS562978A JP S562978 A JPS562978 A JP S562978A JP 7860279 A JP7860279 A JP 7860279A JP 7860279 A JP7860279 A JP 7860279A JP S562978 A JPS562978 A JP S562978A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- methanol
- citronellol
- subjected
- 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
Abstract
PURPOSE: To prepare the titled compound useful as a raw material of perfumery, in high purity and yield, with a short process, without using a large amount of reagents, by the three-step reaction comprising anodic methoxylation citronellol, followed by elimination of methanol and cyclization.
CONSTITUTION: For example, citronellol such as the compound of formula I is subjected to the anodic methoxylation in methanol using an alkali metal salt of an aromatic sulfonic acid (e.g. sodium benzenesulfonate) as a supporting electrolyte to obtain a compound of formula II, which is subjected to the methanol-elimination reaction in the presence of a comple of Pd or Ni [e.g. bis(tri-n-butylphosphinepalladium)] and a base (e.g. sodium methoxide). The compound of formula III thus prepared is cyclized in the presence of an acid, easpecially 20W60wt% sulfuric acid to afford the titled compound such as the compound of formula IV.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7860279A JPS562978A (en) | 1979-06-20 | 1979-06-20 | Preparation of 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran |
| US06/158,810 US4312717A (en) | 1979-06-19 | 1980-06-12 | Process for producing 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran |
| DE8080302027T DE3062269D1 (en) | 1979-06-19 | 1980-06-16 | Processes for producing 2,6-dimethyl-3-alkoxy-oct-1-en-8-ol, dehydrocitronellol and 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran |
| EP80302027A EP0021769B1 (en) | 1979-06-19 | 1980-06-16 | Processes for producing 2,6-dimethyl-3-alkoxy-oct-1-en-8-ol, dehydrocitronellol and 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran |
| US06/289,071 US4340544A (en) | 1979-06-19 | 1981-07-31 | Process for producing 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7860279A JPS562978A (en) | 1979-06-20 | 1979-06-20 | Preparation of 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS562978A true JPS562978A (en) | 1981-01-13 |
| JPS6331469B2 JPS6331469B2 (en) | 1988-06-23 |
Family
ID=13666439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7860279A Granted JPS562978A (en) | 1979-06-19 | 1979-06-20 | Preparation of 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS562978A (en) |
-
1979
- 1979-06-20 JP JP7860279A patent/JPS562978A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6331469B2 (en) | 1988-06-23 |
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