CH125890A - Process for the preparation of 2,6-dioxy-3-benzylbenzoic acid. - Google Patents
Process for the preparation of 2,6-dioxy-3-benzylbenzoic acid.Info
- Publication number
- CH125890A CH125890A CH125890DA CH125890A CH 125890 A CH125890 A CH 125890A CH 125890D A CH125890D A CH 125890DA CH 125890 A CH125890 A CH 125890A
- Authority
- CH
- Switzerland
- Prior art keywords
- dioxy
- acid
- benzylbenzoic acid
- benzylbenzoic
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- RKDMDAVSHRCXQZ-UHFFFAOYSA-N 2-benzylbenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1CC1=CC=CC=C1 RKDMDAVSHRCXQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000645 desinfectant Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 210000002700 urine Anatomy 0.000 claims description 2
- WHUFYYNKCXXKSU-UHFFFAOYSA-N 3-benzylbenzoic acid Chemical compound OC(=O)C1=CC=CC(CC=2C=CC=CC=2)=C1 WHUFYYNKCXXKSU-UHFFFAOYSA-N 0.000 claims 1
- 230000000249 desinfective effect Effects 0.000 claims 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims 1
- 239000000243 solution Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 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 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 2.6-Dioxy-3-benzylbenzoesäure. Es wurde gefunden, dass bei der Behand lung von Benzylresorcin mit Kohlensäure in Gegenwart von Alkalien ein Gemisch der beiden isomeren Dioxybenzylbenzoesäuren entsteht, aus welchem man die 2.6-Di- oxy-3-benzylbenzoesäuTe durch Behandeln mit einem geeigneten Lösungsmittel heraus lösen kann.
Die 2. 6-Dioxy-3-benzylbenzoesäure kri stallisiert in weissen Nadeln vom Schmelz punkt<B>160'.</B> In Alkohol und Äther löst sie sieh leicht. Benzol und Toluol lösen in der Kälte schwer, leichter in der Wärme. Mit Eisenchlorid färbt sich die alkoholische Lösung der 2.6-Dioxy-3-benzylbenzoesäure blau. Sie hat stark desinfizierende Eigen schaften und erscheint im Harn ungepaart. Daher soll sie als inneres Desinfektionsmittel verwendet werden.
Beispiel 'l2,3 Teile Benzylresorcin werden in 200 Teilen absolutem Alkohol gelöst, in einer Wasserstoffatmosphäre mit einer Lö sung von 8,5 Teilen Natrium in 125 Teilen absolutem Alkohol versetzt, der Alkohol hier- auf im Vakuum abd.estilliert, der Rückstand nach Abkühlung langsam in einer Kohlen dioxydatmosphäre auf 120 bis<B>130'</B> erhitzt und vier Stunden bei dieser Temperatur be lassen.
Die Aufarbeitung erfolgt wie bei der p - Bromphenyläthylresorcincarbonsäure durch Einleiten von Kohlensäure in die wäs serige Lösung bis zum Verschwinden der phenolphtaleinalkalischen Reaktion und Ab trennen des unveränderten Ausgangsmaterials. Das nach dem Ansäuern erhaltene Produkt wird in ätherischer Lösung entfärbt, dann aus Benzol umkristallisiert. Die Säure kii- stallisiert in weissen Nadeln vom Schmelz punkt<B>160'</B> und gibt mit Ferrichlorid eine Blaufärbung.
Die Hauptmenge besteht aus 2. 6-Dioxy-3-benzylbenzoesäure.
Process for the preparation of 2,6-dioxy-3-benzylbenzoic acid. It has been found that when benzylresorcinol is treated with carbonic acid in the presence of alkalis, a mixture of the two isomeric dioxybenzylbenzoic acids is formed, from which the 2,6-dioxy-3-benzylbenzoesäuTe can be dissolved out by treatment with a suitable solvent.
2. 6-Dioxy-3-benzylbenzoic acid crystallizes in white needles with a melting point of <B> 160 '. </B> It dissolves easily in alcohol and ether. Benzene and toluene dissolve with difficulty in the cold, more easily in the warm. With ferric chloride, the alcoholic solution of 2,6-dioxy-3-benzylbenzoic acid turns blue. It has strong disinfectant properties and appears unpaired in the urine. Therefore it should be used as an internal disinfectant.
Example 13.3 parts of benzylresorcinol are dissolved in 200 parts of absolute alcohol, a solution of 8.5 parts of sodium in 125 parts of absolute alcohol is added in a hydrogen atmosphere, the alcohol is then distilled off in vacuo, and the residue after cooling slowly heated to 120 to <B> 130 '</B> in a carbon dioxide atmosphere and left at this temperature for four hours.
The work-up takes place as in the case of the p-bromophenylethylresorcine carboxylic acid by introducing carbonic acid into the aqueous solution until the phenolphthalein-alkaline reaction disappears and the unchanged starting material is separated off. The product obtained after acidification is decolorized in an ethereal solution and then recrystallized from benzene. The acid accumulates in white needles with a melting point of <B> 160 '</B> and gives it a blue color with ferric chloride.
The main amount consists of 2.6-dioxy-3-benzylbenzoic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH119581T | 1926-01-06 | ||
| DE125890X | 1926-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH125890A true CH125890A (en) | 1928-05-16 |
Family
ID=25709293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH125890D CH125890A (en) | 1926-01-06 | 1927-05-18 | Process for the preparation of 2,6-dioxy-3-benzylbenzoic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH125890A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2756256A (en) * | 1953-07-09 | 1956-07-24 | Dow Chemical Co | Phenyl dihydroxybenzoic acids |
-
1927
- 1927-05-18 CH CH125890D patent/CH125890A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2756256A (en) * | 1953-07-09 | 1956-07-24 | Dow Chemical Co | Phenyl dihydroxybenzoic acids |
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