📋 Workflow
Full workflow, products add-to-cart directly1
Choose oxidant
15 minChoose the oxidant by substrate (primary/secondary alcohol) and target.
💡 Tip PCC/DMP for primary alcohol→aldehyde, Jones reagent for →acid.
⚠️ Caution Strong oxidants are reactive; mind equivalents and temperature.
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2
Low-temperature addition
30 minDissolve substrate in dry solvent, add oxidant dropwise at low temperature.
💡 Tip Low temperature reduces over-oxidation side reactions.
⚠️ Caution Add slowly to avoid local overheating.
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3
Warm the reaction
1–3 hWarm to room temperature or set point, monitor by TLC until substrate gone.
💡 Tip Stop when the starting spot disappears to avoid over-oxidation.
⚠️ Caution Swern oxidation gives malodorous dimethyl sulfide; ensure ventilation.
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4
Quench & workup
30 minQuench with water/reductant, extract, dry and concentrate.
💡 Tip For DMP, add sodium thiosulfate to reduce excess oxidant.
⚠️ Caution Quench thoroughly to prevent residual oxidant affecting product.
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5
Purify & characterize
1 hPurify by column chromatography, confirm by NMR.
💡 Tip Aldehydes are volatile; concentrate at low temperature.
⚠️ Caution Aldehyde products oxidize to acids in air; process quickly.
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⚠️ 5 Common Beginner Mistakes
- ① Over-oxidation: poor temperature/equivalents control
- ② Residual oxidant: incomplete quench
- ③ Aldehyde further oxidized: product not isolated promptly
- ④ Malodorous gas: insufficient ventilation in Swern
- ⑤ Low yield: loss during workup
❓ FAQ
+How to avoid over-oxidation of alcohols?
Control oxidant equivalents, work at low temperature, monitor by TLC, quench promptly.
+What reagent oxidizes primary alcohol to aldehyde?
PCC or Dess-Martin (DMP) stops at the aldehyde under mild conditions.
+How to remove excess oxidant?
Quench with a reductant (e.g. sodium thiosulfate), then extract.