Bicyclo(2.2.1)heptane-2-methanol → Bicyclo[2.2.1]heptane-2-carbaldehyde

HRID 1767659Notes

Reaction equation

HRID 1767659 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][OH:9].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 21308Bicyclo(2.2.1)heptane-2-methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 86864Bicyclo[2.2.1]heptane-2-carbaldehydeYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 2-norbornylmethanol (0.5 ml; 5.8 mmol) and PCC on Al2O3* in CH2Cl2 (25 ml) was stirred at 2–3° C. for 1 h and then allowed to slowly warm up to rt. The reaction mixture was filtered and the solid material washed with CH2Cl2 (2×25 ml). The combined organic fractions were adsorbed onto silica and chromatographed to give 300 mg (42%) product as an oil. *[see Cheng Y.-S, Liu W.-L. and Chen S.-H., Synthesis, (1980) 223.]

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid material washed with CH2Cl2 (2×25 ml)
  3. customchromatographed

Sources & evidence

ORD record
ord-84d84ca2da8943c9a9d2a897b40ac988
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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