Compounds derived from alkoxyacetic acids
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C9H9IO4
mol.wt. 308.07
Synthesis
OH COCH2OCH3
I HO
-Obtained by iodination of 2,4-dihydroxy-α-methoxyacetophenone with iodine and periodic acid in ethanol for 2 h at r.t. (74%) [21]. m.p. 157-158° [21].
1-(2-Hydroxyphenyl)-2-methoxyethanone [138206-45-8]
C9H10O3
mol.wt. 166.18
Syntheses
OH COCH2OCH3
-Preparation by hydrogenolysis of 2-(benzyloxy)α-methoxyacetophenone (SM) in the presence of Pd/C in ethanol for 1 h in hydrogen atmosphere (96%). SM was obtained by treatment of 2-(benzyloxy)phenylmagnesium bromide with methoxyacetonitrile in THF, first in an ice bath, then stirred for 2 h at r.t. (56%, colourless oil) [1113]. -Also obtained by decomposition of 1-(2-acetoxyphenyl)-2-diazoethanone in methanol with copper bronze (54%). The diazoketone (deep red thick oil) was prepared by reaction of diazomethane with 2-acetoxybenzoyl chloride in ethyl ether [1251]. colourless oil [1113], pale yellow liquid [1251]; b.p.0.6-0.8 76-77° [1251]; NMR [1113], IR [1113], MS [1113].
1H
1-(3-Hydroxyphenyl)-2-methoxyethanone [54794-31-9]
C9H10O3
mol.wt. 166.18
Syntheses
OH
-Refer to: [621] and [1276] (Polish patent). COCH2OCH3
N.B.: K salt [622].
1-(4-Hydroxyphenyl)-2-methoxyethanone [32136-81-5] OH
COCH2OCH3
C9H10O3
mol.wt. 166.18
Syntheses -Obtained by scission of 5-hydroxy-4-(4-hydroxyphenyl) 5H-furan-2-one with potassium hydroxide in methanol at 20° for 24 h (85%) [443]. -Also obtained by catalytic debenzylation of 1-(4-benzyloxyphenyl)-2-methoxyethanone in methanol under hydrogen (5 bars) in the presence of 5% Pd/C for 24 h (81%) [443].
COMPOUNDS DERIVED FROM ALKOXYACETIC ACIDS
123
-Also obtained by methoxylation of the trimethylsilyl enol ether of 4-acetoxyacetophenone (SM) according to the procedure [1034], iodosobenzenediacetate replaced iodosobenzene, followed by hydrolysis of the ester complex formed (40%). SM was prepared in two steps from p-hydroxyacetophenone, namely acetylation, then trimethylsilylation (80%) [360]. -Also obtained by reaction of 2-chloro-1-(4-hydroxyphenyl)ethanone (m.p. 151°) with methanolic sodium methoxide at r.t. for 24 h (90%) [602]. -Also refer to: [3] [403] [473] [665] [1344] [1372]. m.p. 133-135° [602], 128-130° [443]; NMR [443] [602], 13C NMR [443], IR [443] [602], MS [443] [602]. 1H
1-(2,4-Dihydroxyphenyl)-2-methoxyethanone [57280-75-8]
C9H10O4
mol.wt. 182.18
Syntheses
OH
-Obtained by reaction of methoxyacetonitrile with resorcinol and subsequent hydrolysis of the ketimine hydrochloride (m.p. 205-207°) formed (Hoesch reaction) [34] [303] [378] HO [1371]. -Also obtained by decomposition of 1-(2,4-diacetoxyphenyl)-2-diazoethanone in methanol with copper bronze (43%). The diazoketone (brownish yellow glassy solid) was prepared by reaction of diazomethane with 2,4-diacetoxybenzoyl chloride in ethyl ether [1251]. -Also obtained by alkaline degradation of 7-acetoxy-3,4-dimethoxycoumarin (m.p. 123-124°) with sodium hydroxide or sodium carbonate [16]. -Also refer to: [17] [18] [21] [33] [123] [379] [592] [801] [803] [1123] [1154] [1253]. COCH 2 OCH3
m.p. 138-139° [
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