Acetone → cis-Pinanediol

HRID 341966Notes

Reaction equation

HRID 341966 reaction equation
[CH3:1][C:2]1[CH:7]2[C:8]([CH3:10])(C)[CH:5](C2)[CH2:4][CH:3]=1.N1C=CC=CC=1.C[N+]1([O-])[CH2:23][CH2:22][O:21]CC1.CC(C)=[O:27]>>[C@@:22]12([OH:21])[CH2:23][C@@H:3]([C:2]1([CH3:7])[CH3:1])[CH2:4][CH2:5][C:8]2([OH:27])[CH3:10]

Participants

5

Reactant 4

HCID 180AcetoneHCID 1049PyridineHCID 6654(+-)-alpha-PineneHCID 82029Methyl morpholine oxide

Product 1

HCID 70359975cis-Pinanediol

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-24eadf45c8c849a6a1c06f8f116ccb3e
Source dataset
uspto-grants-1999_01
Patent number
US05856497

Reaction notes

Loading…