Compounds derived from S-substituted mercaptoacetic acids
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OH COCH2SCN
Br
mol.wt. 351.02
Br
-Obtained by reaction of ammonium thiocyanate with 3,5,α-tribromo-2-hydroxyacetophenone in aqueous acetone at r.t. for 6 h (69%) [1308]. m.p. 142-143° [1308]; IR [1308].
2-(5-Bromo-2-hydroxyphenyl)-2-oxoethyl thiocyanate [260430-29-3]
C9H6BrNO2S
mol.wt. 272.12
Synthesis
OH COCH2SCN
Br
-Obtained by reaction of ammonium thiocyanate with 5,α-dibromo-2-hydroxyacetophenone in aqueous acetone at r.t. for 6 h (88%) [1308]. m.p. 131-132° [1308]; IR [1308].
1-(2-Hydroxyphenyl)-2-(methylthio)ethanone [56986-82-4]
C9H10O2S
mol.wt. 182.96
Synthesis
OH COCH2SCH3
-Preparation by adding a solution of 15% sodium methylmercaptide to a solution of 2-hydroxy-α-bromoacetophenone in methanol in an ice bath. The reaction mixture was stirred for 30 min at r.t. (98%) [1113].
yellow liquid [1113]; MS [1113]. 1-(2-Hydroxyphenyl)-2-(methylsulfonyl)ethanone [39068-36-5]
C9H10O4S
mol.wt. 214.24
Synthesis
OH COCH2SO2CH3
-Obtained by condensation of methyl 2-hydroxybenzoate with dimethylsulfone carbanion in DMSO (65%) [1162]. m.p. 139-140° [1162].
COMPOUNDS DERIVED FROM S-SUBSTITUTED MERCAPTOACETIC ACIDS
323
1-(3-Hydroxyphenyl)-2-(methylsulfonyl)ethanone [52945-17-2]
C9H10O4S
mol.wt. 214.24
Synthesis
OH
-Obtained by condensation of methyl 3-hydroxybenzoate with dimethylsulfone carbanion in DMSO (60%) [1162]. COCH2SO2CH3
m.p. 168-169° [1162].
1-(4-Hydroxyphenyl)-2-(methylsulfonyl)ethanone [52945-18-3]
C9H10O4S
mol.wt. 214.24
Synthesis
OH
-Obtained by condensation of methyl 4-hydroxybenzoate with dimethylsulfone carbanion in DMSO (58%) [1162]. COCH2SO2CH3
m.p. 173-174° [1162].
2-(3-Bromo-2-hydroxy-5-methylphenyl)-2-oxoethyl thiocyanate C10H8BrNO2S Synthesis
OH Br
mol.wt. 286.15
COCH2SCN
CH3
-Obtained by reaction of ammonium thiocyanate with 3,α-dibromo-2-hydroxy-5-methylacetophenone in aqueous acetone at r.t. for 6 h (66%) [1308]. m.p. 148-149° [1308]; IR [1308].
2-(5-Bromo-2-hydroxy-4-methylphenyl)-2-oxoethyl thiocyanate C10H8BrNO2S Synthesis
OH COCH2SCN CH3 Br
mol.wt. 286.15
-Obtained by reaction of ammonium thiocyanate with 5,α-dibromo-2-hydroxy-4-methylacetophenone in aqueous acetone at r.t. for 6 h (73%) [1308]. m.p. 122-123° [1308]; IR [1308].
324
HYDROXYACETOPHENONES
1-(2-Hydroxy-5-methylphenyl)-2-(methylsulfinyl)ethanone [52159-50-9]
C10H12O3S
mol.wt. 212.27
Synthesis
OH COCH2 S CH3
-Refer to: [316].
O CH3 1-(2,4-Dihydroxy-6-methylphenyl)-2-(methylsulfinyl)ethanone [478795-87-8]
C10H12O4S Synthesis
OH COCH2 S CH3 O CH3
HO
mol.wt. 228.27
-Obtained by reaction of ethyl 2,4-dihydroxy-6-methylbenzoate with sodium methylsulfinylmethide [1178] according to [587]. oil [1178].
1-(2-Hydroxy-3-methoxyphenyl)-2-(methylsulfinyl)ethanone [65220-47-5]
C10H12O4S Synthesis
OH CH3O
mol.wt. 228.27
COCH2 S CH3 O
-Preparation by reaction of methyl 3-methoxysalicylate (methyl 2-hydroxy-3-methoxybenzoate) with methylsulfinyle carbanion, itself obtained from DMSO and sodium hydride (83%) [1000].
m.p. 140-142° [1000]; TLC [1000]. 1-(3-Hydroxy-4-methoxyphenyl)-
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