43166-41-2Relevant articles and documents
SULFINIC ACIDS AND RELATED COMPOUNDS. 22. DERIVATIVES OF 2-HYDROXYETHANE-SULFINIC ACID
Lee, Chew,Stidham, D. Brian,Field, Lamar
, p. 53 - 59 (2007/10/02)
Sodium 2-hydroxyethanesulfinate (3) could be converted to the unstable methyl ester 8 by acidification followed by reaction with diazomethane (although the acid 4, itself, could not be isolated as reported).The ester 8 was esterified with 2,2'-dithioacetyl dichloride (10) to afford the desired convergent synthesis of a disulfide bissulfinate ester (11), but 11 was even less stable than 8; efforts to esterify the sulfinate salt 3 with 10 to give a more stable sulfinate salt counterpart (12) of the ester 11 were unpromising.The salt 12 also was sought by reduction of a sulfonyl chloride 13, which was obtained by coupling 10 with 2-hydroxyethanesulfonyl chloride (2) and for which the structure was confirmed by reaction with p-bromoaniline; 12 evidently was obtained, but greater purity not be obtained than ca. 83-95percent.In other reactions, 2-hydroxyethanesulfonyl chloride (2) reacted with p-bromoaniline, and the hydroxysulfonanilide (6) produced could be esterified with 10 to give 9 by use of special conditions.
