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. Author manuscript; available in PMC: 2014 Apr 5.
Published in final edited form as: J Org Chem. 2013 Mar 18;78(7):3452–3456. doi: 10.1021/jo4001564

Table 2.

Optimization of hydrolysis conditions

graphic file with name nihms455042u3.jpg
entry solvent acid (equiv) T (°C) t (h) yielda
1 EtOH 1M aq H2SO4 (6) rt 8 NR
2 MeOH H2SO4 (6) reflux 1 8 %
3 MeOH 50% aq H2SO4 (6) reflux 0.16 84 %
4 MeOH 50% aq H2SO4 (6) rt 48 19 %
5 MeOH 30% aq H2SO4 (6) rt 1.5 NR
6 THF camphorsulfonic (2) rt 3 NR
7 THF 50% aq H2SO4 (6) 55 3 78 %
8 THF 50% aq H2SO4 (6) rt 24 20 %
a

Isolated yields. Cyclododecanone recovered in comparable yields.