A one‐pot synthesis of (±)‐(ring 13C6)‐mandelic acid

Sarath R. Sirimanne, Donald G. Patterson

Research output: Contribution to journalComment/debate

3 Citations (Scopus)

Abstract

A one‐pot synthesis of (±)‐(ring 13C6)‐mandelic acid is reported. [Ring 13C6]‐benzaldehyde was cyanosilylated with trimethylsilyl cyanide (TMSCN)/Znl2. The resulting cyanosilylated adduct was hydrolyzed with concentrated hydrochloric acid without purification. The workup involves evaporation to dryness and extraction of the (±)‐(ring 13C6)‐mandelic acid with hot benzene. After one crystallization, the synthesis produced an overall yield of 65% of (±)‐(ring 13C6)‐mandelic acid that was about 98% pure by HPLC with UV detection.

Original languageEnglish (US)
Pages (from-to)725-731
Number of pages7
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume33
Issue number8
DOIs
StatePublished - Aug 1993

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Hydrochloric Acid
Crystallization
Benzene
Purification
Evaporation
High Pressure Liquid Chromatography
mandelic acid
trimethylsilyl cyanide
benzaldehyde

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

Sirimanne, Sarath R. ; Patterson, Donald G. / A one‐pot synthesis of (±)‐(ring 13C6)‐mandelic acid. In: Journal of Labelled Compounds and Radiopharmaceuticals. 1993 ; Vol. 33, No. 8. pp. 725-731.
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abstract = "A one‐pot synthesis of (±)‐(ring 13C6)‐mandelic acid is reported. [Ring 13C6]‐benzaldehyde was cyanosilylated with trimethylsilyl cyanide (TMSCN)/Znl2. The resulting cyanosilylated adduct was hydrolyzed with concentrated hydrochloric acid without purification. The workup involves evaporation to dryness and extraction of the (±)‐(ring 13C6)‐mandelic acid with hot benzene. After one crystallization, the synthesis produced an overall yield of 65{\%} of (±)‐(ring 13C6)‐mandelic acid that was about 98{\%} pure by HPLC with UV detection.",
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A one‐pot synthesis of (±)‐(ring 13C6)‐mandelic acid. / Sirimanne, Sarath R.; Patterson, Donald G.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 33, No. 8, 08.1993, p. 725-731.

Research output: Contribution to journalComment/debate

TY - JOUR

T1 - A one‐pot synthesis of (±)‐(ring 13C6)‐mandelic acid

AU - Sirimanne, Sarath R.

AU - Patterson, Donald G.

PY - 1993/8

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N2 - A one‐pot synthesis of (±)‐(ring 13C6)‐mandelic acid is reported. [Ring 13C6]‐benzaldehyde was cyanosilylated with trimethylsilyl cyanide (TMSCN)/Znl2. The resulting cyanosilylated adduct was hydrolyzed with concentrated hydrochloric acid without purification. The workup involves evaporation to dryness and extraction of the (±)‐(ring 13C6)‐mandelic acid with hot benzene. After one crystallization, the synthesis produced an overall yield of 65% of (±)‐(ring 13C6)‐mandelic acid that was about 98% pure by HPLC with UV detection.

AB - A one‐pot synthesis of (±)‐(ring 13C6)‐mandelic acid is reported. [Ring 13C6]‐benzaldehyde was cyanosilylated with trimethylsilyl cyanide (TMSCN)/Znl2. The resulting cyanosilylated adduct was hydrolyzed with concentrated hydrochloric acid without purification. The workup involves evaporation to dryness and extraction of the (±)‐(ring 13C6)‐mandelic acid with hot benzene. After one crystallization, the synthesis produced an overall yield of 65% of (±)‐(ring 13C6)‐mandelic acid that was about 98% pure by HPLC with UV detection.

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