GB560081A - A process for the manufacture of new unsaturated alcohols - Google Patents
A process for the manufacture of new unsaturated alcoholsInfo
- Publication number
- GB560081A GB560081A GB5106/42A GB510642A GB560081A GB 560081 A GB560081 A GB 560081A GB 5106/42 A GB5106/42 A GB 5106/42A GB 510642 A GB510642 A GB 510642A GB 560081 A GB560081 A GB 560081A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphuric acid
- decene
- condensing
- acid
- crotonaldehyde
- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
An alcohol of the formula RR1C=CR11CH (OH)CCR111, wherein R, R1 and R11 are hydrogen or alkyl groups with not more than six carbon atoms and R111 is hydrogen, alkyl groups with not more than four carbon atoms, vinyl, methylvinyl or divinyl, is treated with mineral or organic acids or esterifying derivatives thereof or mineral acid salts, whereby the hydroxy group migrates, and may be to a greater or lesser extent esterified. R and R1 may not both be hydrogen and when one of them is methyl the other, and also R11 and R111 may not all be hydrogen. In examples, the following alcohols and acids are employed: (1) 2-methylpropenylethinylcarbinol and sulphuric acid: (2) 4-ethyloctene-4-in-1-ol-3 and sulphuric acid: (3) 3-methylnonadiene-2 : 7-in-4-ol-6 and sulphuric acid: (4) 2-methyloctadiene-1 : 6-in-3-ol-5- and sulphuric acid: (5) octadiene-1 : 6-in-3-ol-5 and sulphuric acid: (6) decene-8-in-5-ol-7 and sulphuric acid: (7) decene-8-in-5-ol-7 and hydrochloric acid: (8) 3-methylnonadiene-2: 7-in-4-ol-6 and hydrochloric acid: (9) decene-8-in-5-ol-7 and hydrochloric acid: (10) decene-8-in-5-ol-7 and acetic anhydride with potassium acetate: (11) octadiene-1 : 6-in-3-ol-5 and hydrochloric acid: (12) 2-methyloctadiene-1 : 6-in-3-ol-5 and hydrochloric acid. When concentrated hydrochloric or sulphuric acid is used the product is esterified; the product of example (10) is an acetate. The phenylurethane of the product of example 1 is obtained by treatment with phenylisocyanate. 2-Methylpropenylethinylcarbinol may be made by condensing acetylene with 2-methylcrotonaldehyde in liquid ammonia in the presence of sodium. It reacts with phenylisocyanate to give a urethane. 4-Ethyloctene-4-in-1-ol-3 may be made by condensing 2-ethylhexene-2-ol-1 with acetylene in liquid ammonia. It gives a urethane by reacting with a -naphthylisocyanate. 3-Methylnonadiene-2 : 7-in-4-ol-6 may be made by condensing 1 : 2-dimethylvinylacetylene in cooled liquid ammonia with crotonaldehyde dissolved in ether while carefully adding sodium. 2-Methyloctadiene-1 : 6-in-3-ol-5 may be made by condensing methylvinylacetylene with crotonaldehyde in liquid ammonia in the presence of sodium. Octadiene-1 : 6-in-3-ol-5 may be made by mixing an ether solution of vinylacetylene with ethylmagnesium bromide and reacting with crotonaldehyde. Decene-8-in-5-ol-7 may be made by condensing the sodio derivative of hexin-1 with crotonaldehyde.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5106/42A GB560081A (en) | 1942-07-17 | 1942-07-17 | A process for the manufacture of new unsaturated alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5106/42A GB560081A (en) | 1942-07-17 | 1942-07-17 | A process for the manufacture of new unsaturated alcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB560081A true GB560081A (en) | 1944-03-20 |
Family
ID=9789832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5106/42A Expired GB560081A (en) | 1942-07-17 | 1942-07-17 | A process for the manufacture of new unsaturated alcohols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB560081A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2451737A (en) * | 1945-10-18 | 1948-10-19 | Hoffmann La Roche | Process for the manufacture of pentaenes |
| US2451739A (en) * | 1945-10-18 | 1948-10-19 | Hoffmann La Roche | Process for the manufacture of pentaenes |
| US2525672A (en) * | 1947-09-26 | 1950-10-10 | Heilbron Ian Morris | Preparation of alkynylalkenylcarbinols |
-
1942
- 1942-07-17 GB GB5106/42A patent/GB560081A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2451737A (en) * | 1945-10-18 | 1948-10-19 | Hoffmann La Roche | Process for the manufacture of pentaenes |
| US2451739A (en) * | 1945-10-18 | 1948-10-19 | Hoffmann La Roche | Process for the manufacture of pentaenes |
| US2525672A (en) * | 1947-09-26 | 1950-10-10 | Heilbron Ian Morris | Preparation of alkynylalkenylcarbinols |
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