NO136974B - PROCEDURES FOR PREPARING THE DIACETYL DERIVATIVE OF P-METHOXYPHENYL ACETALDEHYDE. - Google Patents
PROCEDURES FOR PREPARING THE DIACETYL DERIVATIVE OF P-METHOXYPHENYL ACETALDEHYDE. Download PDFInfo
- Publication number
- NO136974B NO136974B NO4313/72A NO431372A NO136974B NO 136974 B NO136974 B NO 136974B NO 4313/72 A NO4313/72 A NO 4313/72A NO 431372 A NO431372 A NO 431372A NO 136974 B NO136974 B NO 136974B
- Authority
- NO
- Norway
- Prior art keywords
- procedures
- preparing
- diacetyl derivative
- oxidation
- acetaldehyde
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical class CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 title claims description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 claims description 6
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOAWCBUDPVVPDZ-UHFFFAOYSA-N [acetyloxy-(4-methoxyphenyl)methyl] acetate Chemical compound COC1=CC=C(C(OC(C)=O)OC(C)=O)C=C1 ZOAWCBUDPVVPDZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical compound COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
- 238000007059 Strecker synthesis reaction Methods 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003475 thallium Chemical class 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Den'foreliggende oppfinnelse vedrører en fremgangsmåte for fremstilling av diacetylderivatet av p-metoksyfenylacetaldehyd ved oksydasjon av p-metoksystyren med et metallsalt, og det særegne ved fremgangsmåten i henhold til oppfinnelsen er at oksydasjonen gjennomføres med bly-tetraacetat i eddiksyre. The present invention relates to a method for producing the diacetyl derivative of p-methoxyphenylacetaldehyde by oxidation of p-methoxystyrene with a metal salt, and the peculiarity of the method according to the invention is that the oxidation is carried out with lead tetraacetate in acetic acid.
Fremgangsmåten i henhold til den foreliggende oppfinnelse er således en slags bland-oksydasjon av et umettet aromatisk hydro-karbon for fremstilling av det tilsvarende mettede aldehyd, men det nevnte aldehyd oppnås ved den foreliggende oppfinnelse ikke som sådant, men i form av acetaliseringsproduktet av eddiksyren anvendt som løsningsmiddel for prosessen. The method according to the present invention is thus a kind of mixed oxidation of an unsaturated aromatic hydrocarbon to produce the corresponding saturated aldehyde, but the said aldehyde is obtained in the present invention not as such, but in the form of the acetalization product of the acetic acid used as a solvent for the process.
Fra U.S. patentskrift 3.452.04 7 er oksydasjon av p-metoksystyren From the U.S. patent document 3.452.04 7 is oxidation of p-methoxystyrene
i nærvær av sure thalliumsaltløsninger kjent. Denne omsetning fører til det tilsvarende aldehyd. in the presence of acidic thallium salt solutions known. This reaction leads to the corresponding aldehyde.
Det er nå funnet at en lignende omsetning kan gjennomføres med blytetraacetat som er isoelektronisk med Pd<11>, i et vannfritt medium og i nærvær av eddiksyre, hvorved det finner sted en oksydasjon av metylengruppen til aldehydgruppe. ^Omsetningen er enkel, gir høyt utbytte og de anvendte kjemikalier er lett tilgjengelige. It has now been found that a similar reaction can be carried out with lead tetraacetate, which is isoelectronic with Pd<11>, in an anhydrous medium and in the presence of acetic acid, whereby an oxidation of the methylene group to an aldehyde group takes place. ^The turnover is simple, gives a high yield and the chemicals used are easily available.
Det oppnådde p-metoksybenzylidendiacetat kan direkte underkastes Strecker-reaksjonen for å gi den tilsvarende aminosyre, nemlig p-metoksyf enylalanin, The obtained p-methoxybenzylidene diacetate can be directly subjected to the Strecker reaction to give the corresponding amino acid, namely p-methoxy enylalanine,
Det følgende eksempel tjener til å illustrere oppfinnelsen. The following example serves to illustrate the invention.
Eksempel Example
I en 4-halskolbe forsynt med mekanisk rørverk, termometer, dråpetrakt og som holdes under en nitrogenstrøm oppslemmes 68 g blytetraacetat i 100 ml eddiksyre, 20 g metoksystyren til-dryppes sakte mens temperaturen holdes under 25°C. In a 4-necked flask equipped with mechanical piping, thermometer, dropping funnel and kept under a stream of nitrogen, 68 g of lead tetraacetate are suspended in 100 ml of acetic acid, 20 g of methoxystyrene is slowly added dropwise while the temperature is kept below 25°C.
Etter 2 timer tilsettes 600 ml H,,0. After 2 hours, 600 ml of H 2 O are added.
Diacetylderivåtet av p.metoksyfenylacetaldehyd, det vil si p-metoksybenzyliden-diacetatet, falt ut som en tykk olje. Vannet ble fjernet ved dekantering og oljen ble tørket over natten og det oppnås et utbytte på 31' g. The diacetyl derivative of p-methoxyphenylacetaldehyde, i.e. the p-methoxybenzylidene diacetate, precipitated as a thick oil. The water was removed by decantation and the oil was dried overnight and a yield of 31 g was obtained.
Produktet var delvis krystallinsk. Fra eter-ligroin fikk man The product was partially crystalline. From ether-ligroin one got
en krystallinsk komponent som smeltet ved 52°C. Utbyttet var etter sublimering 91%. a crystalline component which melted at 52°C. The yield after sublimation was 91%.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT31736/71A IT946111B (en) | 1971-11-26 | 1971-11-26 | PROCEDURE FOR THE PREPARATION OF AROMATIC AMINO ACIDS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO136974B true NO136974B (en) | 1977-08-29 |
| NO136974C NO136974C (en) | 1977-12-07 |
Family
ID=11234293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4313/72A NO136974C (en) | 1971-11-26 | 1972-11-24 | PROCEDURES FOR PREPARING THE DIACETYL DERIVATIVE OF P-METHOXYPHENYL ACETALDEHYDE. |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE791781A (en) |
| FR (1) | FR2163015A5 (en) |
| GB (1) | GB1398175A (en) |
| IE (1) | IE38296B1 (en) |
| IT (1) | IT946111B (en) |
| LU (1) | LU66540A1 (en) |
| NL (1) | NL7215785A (en) |
| NO (1) | NO136974C (en) |
-
0
- BE BE791781D patent/BE791781A/en unknown
-
1971
- 1971-11-26 IT IT31736/71A patent/IT946111B/en active
-
1972
- 1972-11-15 IE IE1576/72A patent/IE38296B1/en unknown
- 1972-11-17 GB GB5337172A patent/GB1398175A/en not_active Expired
- 1972-11-22 NL NL7215785A patent/NL7215785A/xx not_active Application Discontinuation
- 1972-11-23 FR FR7241590A patent/FR2163015A5/fr not_active Expired
- 1972-11-24 LU LU66540A patent/LU66540A1/xx unknown
- 1972-11-24 NO NO4313/72A patent/NO136974C/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE791781A (en) | 1973-03-16 |
| NL7215785A (en) | 1973-05-29 |
| DE2257094A1 (en) | 1973-05-30 |
| GB1398175A (en) | 1975-06-18 |
| IE38296L (en) | 1973-05-26 |
| FR2163015A5 (en) | 1973-07-20 |
| IT946111B (en) | 1973-05-21 |
| IE38296B1 (en) | 1978-02-15 |
| LU66540A1 (en) | 1973-02-01 |
| NO136974C (en) | 1977-12-07 |
| DE2257094B2 (en) | 1975-07-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Szarek et al. | Addition of pseudohalogens to unsaturated carbohydrates. III. Synthesis of 3-deoxy-3-C-nitromethyl-D-allose, a branched-chain nitro sugar | |
| US3846490A (en) | Method of producing zeta-aminolevulinic acid hydrochloride | |
| NO136974B (en) | PROCEDURES FOR PREPARING THE DIACETYL DERIVATIVE OF P-METHOXYPHENYL ACETALDEHYDE. | |
| SU499802A3 (en) | The method of obtaining aliphatic-amino acids | |
| JPS5848554B2 (en) | Manufacturing method of nicotinamide | |
| US2459964A (en) | Manufacture of maleamic acid | |
| Erlanger et al. | Phosphorus Pentaoxide as a Reagent in Peptide Synthesis | |
| Fanta | Some 5-Substituted Derivatives of Ethyl 2-Methylnicotinate1 | |
| Jiricny et al. | The conversion of aldehydes and ketones via their 2, 4, 6-tri-isopropylbenzenesulphonyl hydrazones into nitrites containing one additional carbon atom | |
| SU412183A1 (en) | ||
| SU445656A1 (en) | The method of obtaining 4-keto-10a-oxy1,2,3,4,5,6,7,8,8a, 10a-deca-hydroxantenes | |
| SU454737A3 (en) | The method of producing acrylamide or methacrylamide | |
| US961915A (en) | Reduction products of commercial nitrobenzaldehyde. | |
| SU362821A1 (en) | METHOD OF OBTAINING MONOAMIDE OF MALEIC ACID | |
| SU396333A1 (en) | METHOD OF OBTAINING N- (p-OKCIETIL) -DIAZYPIDIHOB | |
| SU118168A1 (en) | Method for producing 1,2-diaminoanthraquinone | |
| Masuzawa et al. | The reaction of C-substituted ethylenediamine with the ester of α-halo acid | |
| US2523746A (en) | Aldehyde products of condensation of acroleins and acylamido malonic and cyanoacetic esters | |
| SU339161A1 (en) | The method of obtaining 5-aminomethylindole or their acyl derivatives | |
| SU548600A1 (en) | The method of obtaining 3,4-xylidine | |
| SU1502558A1 (en) | Method of producing 4-methyl-1-adamantol | |
| SU129018A1 (en) | The method of obtaining derivatives of ferrocene | |
| US2831867A (en) | Process for producing alpha-phenyl succinimides | |
| SU368255A1 (en) | METHOD OF OBTAINING SUBSTITUTED DIBENZO-9-AZABICYCLO- | |
| US2963515A (en) | Process for preparing a |