DE1148535B - Process for the preparation of 1-phenyl-1-hydroxy-2-halo-propanes - Google Patents

Process for the preparation of 1-phenyl-1-hydroxy-2-halo-propanes

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Publication number
DE1148535B
DE1148535B DEG31503A DEG0031503A DE1148535B DE 1148535 B DE1148535 B DE 1148535B DE G31503 A DEG31503 A DE G31503A DE G0031503 A DEG0031503 A DE G0031503A DE 1148535 B DE1148535 B DE 1148535B
Authority
DE
Germany
Prior art keywords
phenyl
hydroxy
propanes
halo
preparation
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.)
Pending
Application number
DEG31503A
Other languages
German (de)
Inventor
Dr Gernot Grimmer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GERNOT GRIMMER DR
Original Assignee
GERNOT GRIMMER DR
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by GERNOT GRIMMER DR filed Critical GERNOT GRIMMER DR
Priority to DEG31503A priority Critical patent/DE1148535B/en
Publication of DE1148535B publication Critical patent/DE1148535B/en
Pending legal-status Critical Current

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Classifications

    • 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
    • C07C29/64—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens
    • C07C29/66—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens by addition of hypohalogenous acids, which may be formed in situ, to carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
    • C07C5/09—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds to carbon-to-carbon double bonds

Description

Verfahren zur Herstellung von 1 -Phenyl- 1 -hydroxy-2-halogen-propanen Die l-Phenyl-l-hydroxy-2-halogen-propane sind wichtige Zwischenprodukte für die Herstellung von Ephedrin und verwandten Körpern. Der Ausdruck »Phenyl« umfaßt dabei auch die substituierten Phenyle. Process for the preparation of 1-phenyl-1-hydroxy-2-halo-propanes The l-phenyl-l-hydroxy-2-halogen-propane are important intermediates for the Manufacture of ephedrine and related bodies. The term "phenyl" includes also the substituted phenyls.

Die bisherigen Synthesen zur Herstellung von Ephedrin und ähnlichen Verbindungen verlaufen über das Phenyl-methyl-diketon oder über das Acyloin. Die Schwierigkeit in der Herstellung dieser Verbindungen liegt darin, daß die Produkte in verschiedenen isomeren Formen vorkommen, die bei den meisten Synthesen nebeneinander entstehen. The previous syntheses for the production of ephedrine and the like Connections run via the phenyl-methyl-diketone or via the acyloin. the The difficulty in preparing these compounds is that the products occur in different isomeric forms, which in most syntheses occur side by side develop.

Es wurde nun gefunden, daß man die 1-Phenyl-1 -hydroxy-2-halogen-propane in der gewünschten Pseudoform erhält, wenn man l-Phenyl-propin-l einer partiellen Reduktion derart unterwirft, daß das entsprechende l-Phenyl-propen-1 entsteht, und an dies Produkt ein Halogenhydrin, vorzugsweise Bromhydrin, anlagert. Bei der Hydrierung entsteht in sehr guter Ausbeute die cis-Form, die bei der Anlagerung des Halogenhydrins die Pseudoverbindung liefert. Diese läßt sich durch Austausch des Halogenatoms durch die Methylamingruppe in das d,l-Ephedrin überführen. It has now been found that 1-phenyl-1-hydroxy-2-halo-propane can be used obtained in the desired pseudo-form if one l-phenyl-propyne-l is a partial Subjects reduction in such a way that the corresponding l-phenyl-propene-1 is formed, and a halohydrin, preferably bromohydrin, is added to this product. In the case of hydrogenation the cis form is produced in very good yield, which occurs when the halohydrin is added on supplies the pseudo connection. This can be done by exchanging the halogen atom convert the methylamine group into the d, l-ephedrine.

Beispiel 1 g l-Phenyl-propin-l werden mit 50 ml Methanol und anschließend mit einer Aufschwemmung von Raney-Nickel in 30 ml KOH (2normal, methanolisch) zugegeben. Vor der Zugabe des l-Phenyl-propins-l soll vorhydriert und eine genügende Zeit gewartet werden. Die Hydriergeschwindigkeit ist anfangs sehr gut und läßt gegen Ende des Verbrauchs der theoretisch errechneten Menge Wasserstoff stark nach, so daß die Reaktion bei der olefinischen Stufe gestoppt werden kann. Example 1 g of l-phenyl-propyne-1 with 50 ml of methanol and then with a suspension of Raney nickel in 30 ml of KOH (2 normal, methanolic) was added. Before adding the l-phenyl-propyn-l, pre-hydrogenate and wait a sufficient time will. The hydrogenation rate is very good at the beginning and can be towards the end of the Consumption of the theoretically calculated amount of hydrogen strongly after, so that the Reaction can be stopped at the olefinic stage.

An das so gebildete l-Phenyl-propen-l wird in an sich bekannter Weise Bromhydrin angelagert. Die Umsetzung verläuft nach folgender Gleichung: 0 CC-CB CH = CH - CH: 4/ H>, ) CH = CHCH3 cis-Form Br + BrOH f CH - CH - CH3 OH ob pseudo-d,l-Form Bromohydrin is added to the l-phenyl-propene-1 thus formed in a manner known per se. The implementation proceeds according to the following equation: 0 CC-CB CH = CH - CH: 4 / H>,) CH = CHCH3 cis form Br + BrOH f CH - CH - CH3 OH whether pseudo-d, l-form

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 1-Phenyl-1 -hydroxy-2-halogen-propanen, dadurch gekennzeichnet, daß ein l-Phenyl-propin-l in an sich bekannter Weise zum entsprechenden 1-Phenylpropen-l partiell reduziert und an das so erhaltene Produkt ein Halogenhydrin, vorzugsweise Bromhydrin, in an sich bekannter Weise angelagert wird.PATENT CLAIM: Process for the production of 1-phenyl-1-hydroxy-2-halogen-propanes, characterized in that a l-phenyl-propyne-l in a known manner for corresponding 1-phenylpropene-l partially reduced and to the product thus obtained a halohydrin, preferably bromohydrin, added on in a manner known per se will.
DEG31503A 1961-01-31 1961-01-31 Process for the preparation of 1-phenyl-1-hydroxy-2-halo-propanes Pending DE1148535B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEG31503A DE1148535B (en) 1961-01-31 1961-01-31 Process for the preparation of 1-phenyl-1-hydroxy-2-halo-propanes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEG31503A DE1148535B (en) 1961-01-31 1961-01-31 Process for the preparation of 1-phenyl-1-hydroxy-2-halo-propanes

Publications (1)

Publication Number Publication Date
DE1148535B true DE1148535B (en) 1963-05-16

Family

ID=7124235

Family Applications (1)

Application Number Title Priority Date Filing Date
DEG31503A Pending DE1148535B (en) 1961-01-31 1961-01-31 Process for the preparation of 1-phenyl-1-hydroxy-2-halo-propanes

Country Status (1)

Country Link
DE (1) DE1148535B (en)

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