Béhal-Sommelet rearrangement

The Béhal-Sommelet rearrangement is a name reaction in organic chemistry . Auguste Béhal (1859–1941) and Marcel Sommelet (1877–1952) reported this reaction for the first time in 1904.

Overview reaction

In the Béhal-Sommelet rearrangement, a β-hydroxyalkyl ether (R = alkyl or aryl radical ) reacts with acid catalysis to form an aldehyde :

Reaction mechanism

In the proposed reaction mechanism, the β-hydroxyalkyl ether 1 is first converted into the enol ether 2 under acid catalysis with elimination of water . 2 is then converted to the desired aldehyde 3 with the aid of an acid and with elimination of ethanol :

modification

Phenyl-β-hydroxylalkyl ethers can also be used as β-hydroxyalkyl ethers.

application

The Béhal-Sommelet rearrangement is a widely applicable method for the synthesis of α-substituted aldehydes.

Individual evidence

↑ ^a ^b ^c ^d ^e Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , doi : 10.1002 / 9780470638859 .
↑ R. Stoermer: Synthesis of aldehydes and ketones from asymmetrically disubstituted ethylene glycols and their ethers . In: Reports of the German Chemical Society . tape 39 , no. 2 , 1906, p. 2288-2306 , doi : 10.1002 / cber.190603902205 .
↑ Douglas Currell, Arthur Fry: A Tracer Study of the Mechanism of the Conversion of Methallyl Alcohol to Isobutyraldehyde1,2 . In: Journal of the American Chemical Society . tape 78 , no. 17 , September 1, 1956, p. 4377-4379 , doi : 10.1021 / ja01598a050 .
↑ LEE IRVIN SMITH, JOSEPH NICHOLS: THE SYNTHESIS OF ALDEHYDES FROM GRIGNARD REAGENTS. II. POLYMETHYLBENZALDEHYDE . In: The Journal of Organic Chemistry . tape 06 , no. 4 , July 1, 1941, p. 489-506 , doi : 10.1021 / jo01204a003 .

[:0-1] Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , doi : 10.1002 / 9780470638859 .

[2] R. Stoermer: Synthesis of aldehydes and ketones from asymmetrically disubstituted ethylene glycols and their ethers . In: Reports of the German Chemical Society . tape 39 , no. 2 , 1906, p. 2288-2306 , doi : 10.1002 / cber.190603902205 .

[3] Douglas Currell, Arthur Fry: A Tracer Study of the Mechanism of the Conversion of Methallyl Alcohol to Isobutyraldehyde1,2 . In: Journal of the American Chemical Society . tape 78 , no. 17 , September 1, 1956, p. 4377-4379 , doi : 10.1021 / ja01598a050 .

[4] LEE IRVIN SMITH, JOSEPH NICHOLS: THE SYNTHESIS OF ALDEHYDES FROM GRIGNARD REAGENTS. II. POLYMETHYLBENZALDEHYDE . In: The Journal of Organic Chemistry . tape 06 , no. 4 , July 1, 1941, p. 489-506 , doi : 10.1021 / jo01204a003 .