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Synthesis of methyl (±)‐2,3‐ O ‐isopropylideneglycerate by electrochemical oxidation of (±)‐1,2‐ O ‐isopropylideneglycerol
Author(s) -
Schwarz KarlHeinz,
Kleiner Katharina,
Ludwig Ralf,
Schrötter Eberhard,
Schick Hans
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910191
Subject(s) - chemistry , yield (engineering) , electrochemistry , potassium hydroxide , potassium carbonate , acetone , inorganic chemistry , salt (chemistry) , boiling , sodium hydroxide , oxide , anodic oxidation , dimethyl sulfate , nuclear chemistry , sodium , potassium , silver oxide , sodium sulfate , electrode , organic chemistry , materials science , metallurgy
The anodic oxidation of (±)‐1,2‐ O ‐isopropylideneglycerol at a silver/silver oxide electrode with a controlled potential of +0.9 V vs. SCE in 2.5 N sodium hydroxide affords sodium (±)‐2,3‐ O ‐isopropylideneglycerate in a yield of 75%. Treatment of this salt with dimethyl sulfate and potassium carbonate in boiling acetone leads to methyl (±)‐2,3‐ O ‐isopropylideneglycerate in a yield of 81%.