2013•Fine Chemical IntermediatesRequires access

The Preparation of D-4-Hydroxyphenylglycine

Dengke Liu

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Abstract

DL-p-Hydroxyphenylglycine was synthesized from phenol and glyoxylic acid and converted into its methyl ester by reaction with SOCl2 and methanol.After treatment with(+)-tartaric acid,the methyl D-p hydroxyphenylglycinate(+)-tartrate was obtained.The tartrate was hydrolyzed in alkaline solution and then neutralized to form the D-hydroxyphenylglycine.The L-hydroxyphenylglycine was racemized in methanol with salicylaldehyde.The resolution yield was up to 70.7% with 99.8%e.e.

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What this paper is about

DL-p-Hydroxyphenylglycine was synthesized from phenol and glyoxylic acid and converted into its methyl ester by reaction with SOCl2 and methanol.After treatment with(+)-tartaric acid,the methyl D-p hydroxyphenylglycinate(+)-tartrate was obtained.The tartrate was hydrolyzed in alkaline solution and then neutralized to form the D-hydroxyphenylglycine.The L-hydroxyphenylglycine was racemized in methanol with salicylaldehyde.The resolution yield was up to 70.7% with 99.8%e.e.

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Available abstract

DL-p-Hydroxyphenylglycine was synthesized from phenol and glyoxylic acid and converted into its methyl ester by reaction with SOCl2 and methanol.After treatment with(+)-tartaric acid,the methyl D-p hydroxyphenylglycinate(+)-tartrate was obtained.The tartrate was hydrolyzed in alkaline solution and then neutralized to form the D-hydroxyphenylglycine.The L-hydroxyphenylglycine was racemized in methanol with salicylaldehyde.The resolution yield was up to 70.7% with 99.8%e.e.

Key concepts: Chemistry, Salicylaldehyde, Tartrate, Glyoxylic acid, Methanol, Yield (engineering), Hydrolysis, Phenol

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