GB973844A - Process for the production of 10-hydroxyhexadec-7-yne-1-oic acid - Google Patents
Process for the production of 10-hydroxyhexadec-7-yne-1-oic acidInfo
- Publication number
- GB973844A GB973844A GB19490/63A GB1949063A GB973844A GB 973844 A GB973844 A GB 973844A GB 19490/63 A GB19490/63 A GB 19490/63A GB 1949063 A GB1949063 A GB 1949063A GB 973844 A GB973844 A GB 973844A
- Authority
- GB
- United Kingdom
- Prior art keywords
- yne
- hydroxyhexadec
- oic acid
- chlorohept
- chloro
- 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
- NLUJKSFIHSXCDQ-UHFFFAOYSA-N 10-hydroxyhexadec-7-ynoic acid Chemical compound OC(CC#CCCCCCC(=O)O)CCCCCC NLUJKSFIHSXCDQ-UHFFFAOYSA-N 0.000 title abstract 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- JHURUSBTPUNQSC-UHFFFAOYSA-N 7-chlorohept-1-yne Chemical compound ClCCCCCC#C JHURUSBTPUNQSC-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- -1 iodo compound Chemical class 0.000 abstract 2
- KDIZIOCCMMRKDU-UHFFFAOYSA-N 15-chloropentadec-9-yn-7-ol Chemical compound ClCCCCCC#CCC(CCCCCC)O KDIZIOCCMMRKDU-UHFFFAOYSA-N 0.000 abstract 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
10-Hydroxyhexadec-7-yne-1-oic acid is produced by converting 7-chlorohept-1-yne into an organo-metallic compound with n-butyl lithium, reacting this with 1, 2-epoxyoctane to give 1-chloro-9-hydroxypentadec-6-yne, converting this into the corresponding 1-iodo compound with sodium iodide, reacting the iodo compound with excess sodium or potassium cyanide to give 10-hydroxyhexadec-7-yne-1-oic acid nitrile which is then hydrolysed with an aqueous alcoholic solution of an alkali metal hydroxide, the whole synthesis being carried out in the absence of oxygen. The 7-chlorohept-1-yne may be obtained from 1-chloro-5-iodobutane and sodium acetylide in liquid ammonia.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF36849A DE1189988B (en) | 1962-05-19 | 1962-05-19 | Process for the preparation of 10-hydroxy-7-hexadecyne-1-acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB973844A true GB973844A (en) | 1964-10-28 |
Family
ID=7096634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19490/63A Expired GB973844A (en) | 1962-05-19 | 1963-05-16 | Process for the production of 10-hydroxyhexadec-7-yne-1-oic acid |
Country Status (3)
| Country | Link |
|---|---|
| CH (2) | CH428706A (en) |
| DE (1) | DE1189988B (en) |
| GB (1) | GB973844A (en) |
-
1962
- 1962-05-19 DE DEF36849A patent/DE1189988B/en active Pending
-
1963
- 1963-05-07 CH CH574163A patent/CH428706A/en unknown
- 1963-05-07 CH CH1754566A patent/CH429700A/en unknown
- 1963-05-16 GB GB19490/63A patent/GB973844A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH429700A (en) | 1967-02-15 |
| CH428706A (en) | 1967-01-31 |
| DE1189988B (en) | 1965-04-01 |
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