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8th August 2013 @ 09:02
Aew: 60-80

Resynthesis of glycolic acid acetonide. See also Synthesis of Glycolic Acid Acetonide (PMY 7-1).

Started 11.30 am Thursday 15th August

Condensation of acetone and glycolic acid to give the protected/activated glycolic acid acetonide for further side chain elaboration.


Glycolic acid (2.05 g, 27.0 mmol, 1 equiv.) was stirred in acetone (40 mL) with a few crystals of p-TSA for 1 hour. NaHCO3 (approx 1 g) was added and dried (MgSO4) before filtration and partially concentration to a colourless oil. 

NMR:

 

References:

 

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