Alcohol reaction with thionyl chloride

Thionyl chloride reacts with alcohols to give alkyl chlorides The inorganic byprod nets m the reaction sulfur dioxide and hydrogen chloride are both gases at room tern perature and are easily removed making it an easy matter to isolate the alkyl chloride... 

Carboxylic acids react with thionyl chloride to form acid chlorides. Reaction with alcohols gives esters, and with amines, amides are formed. 

Thionyl chloride reacts with alcohols to give alkyl chlorides. The reaction is typically carried out in the presence of pyridine, which acts both as solvent and a base that reacts with the HCl that is produced. 

Now let s draw the forward scheme. The primary alcohol is oxidized to the carboxyhc acid, and subsequently converted to the acid chloride upon treatment with thionyl chloride. Reaction with lithium diethyl cuprate then produces the desired ketone. 

By the action of thionyl chloride upon the alcohol alone or mixed with pyridine (to absorb the hydrogen chloride formed in the reaction), for example ... 

Diorgano Sulfites. Symmetrical or mixed dialkyl sulfites ate prepared by the stepwise reaction of thionyl chloride either with two molecules of an alcohol or with stoichiometric quantities of two alcohols in pyridine (105). 

Because tertiary alcohols are so readily converted to chlorides with hydrogen chloride, thionyl chloride is used mainly to prepare primary and secondary alkyl chlorides. Reactions with thionyl chloride are nonrrally carried out in the presence of potassium carbonate or the weak organic base pyridine. 

The initial medicinal chemistry route to the azabicyclo[3.3.0]octane-3-carboxylic acid produced the azabicyclo system in a diastereoselective but racemic manner, and required a classical resolution to achieve enantioenriched material (Teetz et al., 1984a, b 1988). Reaction of (R)-methyl 2-acetamido-3-chloropropanoate (43) and 1-cyclopentenylpyrrolidine (44) in DMF followed by an aqueous acidic work-up provided racemic keto ester 45 in 84% yield (Scheme 10.11). Cyclization of 45 in refluxing aqueous hydrochloric acid provided the bicyclic imine, which was immediately reduced under acidic hydrogenation conditions. The desired cis-endo product 46 was obtained upon recrystaUization. The acid was protected as the benzyl ester using thionyl chloride and benzyl alcohol, providing subunit 47 as the racemate. Resolution of 47 was accomplished by crystallization with benzyloxy-carbonyl-L-phenylalanine or L-dibenzoyl-tartaric acid. 

Indeed, if methanol is heated with fuming sulfuric acid, dimethyl sulfate, CH30(S02)0CH3, is obtained but other alcohols are better converted to dialkyl sulfates by oxidation of the corresponding dialkyl sulfites formed by the reaction of 1 mole of thionyl chloride (SOCl2) with 2 moles of the alcohol ... 

Some general conclusions can be drawn from the data in Table 30. Thionyl chloride reacts with allylic alcohols by the mechanism whenever the alternative Sn process would require attack on a more hindered site c/. p. 40). In the absence of this restriction, however, the Sm reaction seems to be preferred, as it is for simple aliphatic compounds [ig]. The behaviour of the 4j8-hydroxy AS- (5) and 6jS-hydroxy-A - (6) compounds is clearly of type, despite any steric opposition... 

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