BE885030A - PROCESS FOR THE PREPARATION OF 1- (P-HYDROXY-PHENYL) -2-METHOXYETHANE - Google Patents

PROCESS FOR THE PREPARATION OF 1- (P-HYDROXY-PHENYL) -2-METHOXYETHANE Download PDF

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Publication number
BE885030A
BE885030A BE0/201947A BE201947A BE885030A BE 885030 A BE885030 A BE 885030A BE 0/201947 A BE0/201947 A BE 0/201947A BE 201947 A BE201947 A BE 201947A BE 885030 A BE885030 A BE 885030A
Authority
BE
Belgium
Prior art keywords
emi
methoxyethane
preparation
hydroxy
phenyl
Prior art date
Application number
BE0/201947A
Other languages
French (fr)
Inventor
D M Knott
H K Lundmark
K Sjoberg
B E Akermark
Original Assignee
Astra Pharma Prod
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 Astra Pharma Prod filed Critical Astra Pharma Prod
Publication of BE885030A publication Critical patent/BE885030A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
    • C07C43/1782—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

   <EMI ID=1.1> 

  
éthane.

  
La présente invention concerne an procédé pour

  
 <EMI ID=2.1> 

  
méthoxyéthane; selon des voies de procédé plus efficaces. 

  
 <EMI ID=3.1> 

  
moyen d'une réaction de Grignard suivie de bromation, déméthylation, et méthoxylation.

  
Le composé 1- (p-hydroxyphényl) -2-méthoxyéthane est employé comme produit intermédiaire dans la préparation

  
 <EMI ID=4.1> 

  
Il a été maintenant trouvé de manière suprenante que le p-hydroxystyrène peut être employé comme matériau de départ.

  
Ainsi, le p-hydroxystyrène pourra être transformé

  
 <EMI ID=5.1> 

  
acétylation du phénol en 1- (p-acétoxyphényl) -2-bromcéthane,

  
ce qui donne le composé désiré après réaction avec le méthoxyde&#65533;

  
2)époxylation de p-hydroxystyrène en utilisant

  
 <EMI ID=6.1> 

  
ou méthanol ; 

  
3) addition catalysée par métal de méthanol, en p-hydroxystyrène, de préférence par utilisation de palladium sous forme de Pd/C;

  
4) le p-hydroxystyrène est traité avec un. acide

  
 <EMI ID=7.1>   <EMI ID=8.1> 

  
le borotrifluorure, le chlorure d'aluminium, le tétrachlorure d'étain et le tétrachlorure de titane. Les acides peuvent

  
 <EMI ID=9.1> 

  
dans du méthanol ensemble avec une base telle par exemple triéthylamine, diméthylaniline, on pyridine à des températures 

  
 <EMI ID=10.1> 

  
trifluoroacétique et 70 gr. d'acide acétique à -20[deg.]C. Après  1 heure à -20[deg.]C, le mélange de réaction est déversé dans un

  
 <EMI ID=11.1> 

  
à -20[deg.]C. Après 30 minutée, on a ajouté 5 litres d'eau et le

  
 <EMI ID=12.1>  

  
 <EMI ID=13.1> 



   <EMI ID = 1.1>

  
ethane.

  
The present invention relates to a method for

  
 <EMI ID = 2.1>

  
methoxyethane; according to more efficient process lines.

  
 <EMI ID = 3.1>

  
by means of a Grignard reaction followed by bromination, demethylation, and methoxylation.

  
The compound 1- (p-hydroxyphenyl) -2-methoxyethane is used as an intermediate product in the preparation

  
 <EMI ID = 4.1>

  
It has now been surprisingly found that p-hydroxystyrene can be used as a starting material.

  
Thus, p-hydroxystyrene can be transformed

  
 <EMI ID = 5.1>

  
acetylation of phenol in 1- (p-acetoxyphenyl) -2-bromcethane,

  
which gives the desired compound after reaction with the methoxide #

  
2) epoxylation of p-hydroxystyrene using

  
 <EMI ID = 6.1>

  
or methanol;

  
3) metal-catalyzed addition of methanol, to p-hydroxystyrene, preferably by using palladium in the form of Pd / C;

  
4) p-hydroxystyrene is treated with a. acid

  
 <EMI ID = 7.1> <EMI ID = 8.1>

  
borotrifluoride, aluminum chloride, tin tetrachloride and titanium tetrachloride. Acids can

  
 <EMI ID = 9.1>

  
in methanol together with a base such as for example triethylamine, dimethylaniline, pyridine is at temperatures

  
 <EMI ID = 10.1>

  
trifluoroacetic and 70 gr. acetic acid at -20 [deg.] C. After 1 hour at -20 ° C., the reaction mixture is poured into a

  
 <EMI ID = 11.1>

  
at -20 [deg.] C. After 30 minutes, 5 liters of water were added and the

  
 <EMI ID = 12.1>

  
 <EMI ID = 13.1>

Claims (1)

2. Procédé selon la revendication 1, caractérisé 2. Method according to claim 1, characterized en ce que le matériau de départ est traité avec un acide in that the starting material is treated with an acid fort et est laissé ensuite réagir avec du méthanol on méthoxyde. <EMI ID=14.1> strong and is then allowed to react with methanol or methoxide. <EMI ID = 14.1> et on le fait ensuite réagir avec du méthanol ou méthoxyde. and then reacted with methanol or methoxide. 6. Procédé selon la revendication 1, caractérisé 6. Method according to claim 1, characterized <EMI ID=15.1> <EMI ID = 15.1> au moyen d'un catalyseur métallique. using a metal catalyst. 7. Produite obtenue par le procédé selon n'importe laquelle des revendications 1 à 6. 7. Product obtained by the process according to any one of claims 1 to 6.
BE0/201947A 1979-09-25 1980-09-02 PROCESS FOR THE PREPARATION OF 1- (P-HYDROXY-PHENYL) -2-METHOXYETHANE BE885030A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE7907957A SE7907957L (en) 1979-09-25 1979-09-25 PROCESS OF PREPARING 1 (P-HYDROXIFENYL) -2-METOXYETANE

Publications (1)

Publication Number Publication Date
BE885030A true BE885030A (en) 1980-12-31

Family

ID=20338897

Family Applications (1)

Application Number Title Priority Date Filing Date
BE0/201947A BE885030A (en) 1979-09-25 1980-09-02 PROCESS FOR THE PREPARATION OF 1- (P-HYDROXY-PHENYL) -2-METHOXYETHANE

Country Status (2)

Country Link
BE (1) BE885030A (en)
SE (1) SE7907957L (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5124489A (en) * 1989-12-14 1992-06-23 Hoechst Celanese Corporation Process for preparing phenethanol ethers by the reduction of corresponding phenylglyoxal acetals
BE1007421A3 (en) * 1993-08-20 1995-06-13 Tessenderlo Chem Nv Method for the selective alkylation's of an aliphatic alcohol from a phenolcompound

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5124489A (en) * 1989-12-14 1992-06-23 Hoechst Celanese Corporation Process for preparing phenethanol ethers by the reduction of corresponding phenylglyoxal acetals
BE1007421A3 (en) * 1993-08-20 1995-06-13 Tessenderlo Chem Nv Method for the selective alkylation's of an aliphatic alcohol from a phenolcompound

Also Published As

Publication number Publication date
SE7907957L (en) 1981-03-26

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