I am trying to do a reduction of 2,5-dihydroxybenzaldehyde using NaBH4 in ethanol. However, I am getting extremely poor results. My procedure is pretty standard:
1 molar equivalent of 2,5-dihydroxybenzaldehyde and 1 molar equivalent of NaBH4 stirred together in 95% ethanol for 20 minutes. Stop reaction with 1 molar equivalent of HCl (0.4M). Extract with water and ethyl acetate. Dry with MgSO4. Scale = 0.25 g 2,5-dihydroxybenzaldehyde.
I did a H NMR of the product. Looked like the sample was contaminated. Repeated reaction. Results are very similar. Looked for the product using TLC (ethyl acetate as solvent) and got streaks instead of spots.
Any suggestion of what is wrong with my procedure? I am unsure about my use of ethyl acetate.