GB285156A - Process for the preparation of vanillin and i-vanillin - Google Patents
Process for the preparation of vanillin and i-vanillinInfo
- Publication number
- GB285156A GB285156A GB2852126A GB2852126A GB285156A GB 285156 A GB285156 A GB 285156A GB 2852126 A GB2852126 A GB 2852126A GB 2852126 A GB2852126 A GB 2852126A GB 285156 A GB285156 A GB 285156A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isoeugenol
- isochavibetol
- mixture
- vanillin
- veratrol
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
- C07C47/58—Vanillin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
285,156. Boedecker, F. Nov. 12, 1926. Vanillin and isovanillin are prepared by treating safrol or isosafrol at a high temperature with an alcoholic alkali and methylating the product of reaction to form a mixture of the m- and palkoxymethyl ethers which are then heated with acids to form isoeugenol and isochavibetol, which are oxidized to the aldehydes and separated in known manner. Alternatively, the mixture of isoeugenol and isochavibetol may be separated before oxidation, or may be treated so as to convert it wholly into one or other of these cornpounds. In examples, (1) safrol is heated under pressure with methyl alcoholic notash and the product is methylated with dimethyl sulphate and saponified, giving a mixture of isochavibetol and isoeugenol which are oxidized to isovanillin and vanillin and separated. The mixture of isochavibetol and isoeugenol can also be worked up almost completely into isoeugenol or vanillin bv freezing out the isochavibetol and methylating it to produce propenyl-3.4-veratrol, which if heated with alkali forms a mixture of isoeugenol and isochavibetol, the latter being extracted and added to the next batch. The isoeugenol is obtained from the filtrate by forming the benzoyl or nitrobenzoyl compounds, the acidyl compounds of isoeugenol being less soluble than those of isochavibetol. If it is desired to produce isochavibetol or isovanillin alone, the isoeugenol instead of the isochavibetol is converted into propenyl-3.4-veratrol. (2) A mixture of isochavibetol and isoeugenol obtained as above is mixed with hexahydrotoluene, and on standing in the cold isochavibetol crystallizes out; the mother liquor freed from solvent is distilled in vacuo giving mainly isoeugenol, and on treating this with benzoyl chloride isoeugenol benzoate is obtained. The isochavibetol is converted by boiling in alcoholic lye with halogen methyl into propenyl- 3.4-veratrol and this on heating with alcohol and alkali under pressure gives a mixture of isoeugenol and isochavibetol which is worked up as before. The isoeugenol may be purified by means of its sodium salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2852126A GB285156A (en) | 1926-11-12 | 1926-11-12 | Process for the preparation of vanillin and i-vanillin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2852126A GB285156A (en) | 1926-11-12 | 1926-11-12 | Process for the preparation of vanillin and i-vanillin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB285156A true GB285156A (en) | 1928-02-13 |
Family
ID=10276934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2852126A Expired GB285156A (en) | 1926-11-12 | 1926-11-12 | Process for the preparation of vanillin and i-vanillin |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB285156A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105712859A (en) * | 2014-12-05 | 2016-06-29 | 中国石油天然气股份有限公司 | Centrifugal extraction method of isovanillin |
-
1926
- 1926-11-12 GB GB2852126A patent/GB285156A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105712859A (en) * | 2014-12-05 | 2016-06-29 | 中国石油天然气股份有限公司 | Centrifugal extraction method of isovanillin |
| CN105712859B (en) * | 2014-12-05 | 2018-02-02 | 中国石油天然气股份有限公司 | Centrifugal extraction method of isovanillin |
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