Dimethyl Sulfoxide → Oxypinocamphone

HRID 341967Notes

Reaction equation

HRID 341967 reaction equation
[C@@:1]12(O)[CH2:9][C@@H:5]([C:6]1([CH3:8])[CH3:7])[CH2:4][CH2:3][C:2]2([OH:11])[CH3:10].CS(C)=[O:15].N1C=CC=CC=1>C(N(CC)CC)C>[OH:11][C:2]1([CH3:10])[C:3](=[O:15])[CH2:4][CH:5]2[CH2:9][CH:1]1[C:6]2([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 70359975cis-Pinanediol

Product 1

HCID 112005Oxypinocamphone

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A process for producing 2-hydroxy-3-pinanone, comprising the steps of reacting α-pinene with catalytic potassium osmate in solution of pyridine, N-methylmorpholine-N-oxide and aqueous acetone to produce cis-pinanediol; and thereafter oxidizing said cis-pinanediol with DMSO activated by pyridine.SO3 and triethylamine in an appropriate solvent to produce 2-hydroxy-3-pinanone.

Sources & evidence

ORD record
ord-47f4aeff92dd4566b0fb33b3bc57e54f
Source dataset
uspto-grants-1999_01
Patent number
US05856497

Reaction notes

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