GB948714A - Preparation and use of grignard reagents - Google Patents

Preparation and use of grignard reagents

Info

Publication number
GB948714A
GB948714A GB2787462A GB2787462A GB948714A GB 948714 A GB948714 A GB 948714A GB 2787462 A GB2787462 A GB 2787462A GB 2787462 A GB2787462 A GB 2787462A GB 948714 A GB948714 A GB 948714A
Authority
GB
United Kingdom
Prior art keywords
grignard
titanium
acid
alkyl
ethers
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
Application number
GB2787462A
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.)
General Electric Co
Original Assignee
General Electric Co
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 General Electric Co filed Critical General Electric Co
Publication of GB948714A publication Critical patent/GB948714A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
    • C07F3/02—Magnesium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis

Abstract

Grignard reagents of formula R-C2H4-MgX are made by reacting in a Grignard solvent medium an olefine of formula R-CH=CH2 with an alkyl Grignard reagent of formula R1-MgX in the presence of a halide, alkoxide or aryloxide of titanium or zirconium, where R is a monovalent radical free of substituents reactive to said alkyl Grignard reagent, R1 is an alkyl radical having at least 2 carbon atoms and having at least one hydrogen atom on the b -carbon atom, and X is a halogen. The expression "Grignard solvent medium" includes the dialkyl ethers, cyclic ethers e.g. dioxane and tetrahydrofuran, alkyl aryl ethers e.g. anisole and phenetole, dimethyl and dibutyl ethers of ethylene glycol, the diethyl ether of diethylene glycol and pyridine. The titanium and zirconium catalysts include the oxyhalides and halides in which organic radicals are directly attached to the titanium and zirconium atoms e.g. dicyclopentadienyl titanium dichloride, "Alkoxides" and "aryloxides" include compounds containing organic groups attached directly to the metal atom such as diphenyl titanium diisopropoxide, and monomeric and polymeric titanates and zirconates. The process is carried out by preparing the alkyl Grignard compound conventionally in the selected solvent, adding the olefin, cooling to below room temperature, adding the catalyst and allowing the temperature to rise, if necessary to 200 DEG C. by applied heating. The Grignard compounds so prepared may be used to prepare other compounds by reaction with carbon dioxide, aldehydes, ketones, water, organic orthoformates &c. The following are prepared in the examples: Example 2,p-methoxyhydrotropic acid; Example 3, b -cyclohexylpropionic acid; Example 4, octane; Example 5, pelargonic diethyl acetal; Example 6, 1-hexylcyclohexanol; Example 7, methyl pelargonate; Example 8, b -(D 3-cyclohexanyl) propionic acid; Example 9, 1-hexanol; Example 14, 6-methyl-2-heptanol; Example 15, g -phenylbutyric acid; Example 16, b -(D 3-cyclohexenyl) ethanol; Example 17, 2-methyldecanol-2; Example 18, hydratropic acid.
GB2787462A 1961-07-19 1962-07-19 Preparation and use of grignard reagents Expired GB948714A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US12509461A 1961-07-19 1961-07-19

Publications (1)

Publication Number Publication Date
GB948714A true GB948714A (en) 1964-02-05

Family

ID=22418153

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2787462A Expired GB948714A (en) 1961-07-19 1962-07-19 Preparation and use of grignard reagents

Country Status (2)

Country Link
CH (1) CH455766A (en)
GB (1) GB948714A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0820809A1 (en) * 1995-03-10 1998-01-28 Nissan Chemical Industries, Limited Titanium catalyst, organotitanium reaction reagent, processes for producing these, and method of reaction using these
WO2000002928A1 (en) * 1998-07-09 2000-01-20 Basf Aktiengesellschaft Method for the stereoselective production of grignard compounds and use thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0820809A1 (en) * 1995-03-10 1998-01-28 Nissan Chemical Industries, Limited Titanium catalyst, organotitanium reaction reagent, processes for producing these, and method of reaction using these
EP0820809A4 (en) * 1995-03-10 2000-06-28 Nissan Chemical Ind Ltd Titanium catalyst, organotitanium reaction reagent, processes for producing these, and method of reaction using these
US6867161B1 (en) 1995-03-10 2005-03-15 Nissan Chemical Industries, Ltd. Titanium catalyst and organotitanium reacting reagent, production thereof, and reaction thereby
WO2000002928A1 (en) * 1998-07-09 2000-01-20 Basf Aktiengesellschaft Method for the stereoselective production of grignard compounds and use thereof
US6432326B1 (en) 1998-07-09 2002-08-13 Basf Aktiengesellschaft Method for the stereoselective production of grignard compounds and use thereof

Also Published As

Publication number Publication date
CH455766A (en) 1968-05-15

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