Acetone → cis-Pinanediol

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

Reactant 4

HCID 180Acetone

HCID 1049Pyridine

HCID 6654(+-)-alpha-Pinene

HCID 82029Methyl morpholine oxide

Product 1

HCID 70359975cis-Pinanediol

Procedure

reacting α-pinene with catalytic potassium osmate in a solution of pyridine, N-methylmorpholine-N-oxide and aqueous acetone to form cis-pinanediol;

Sources & evidence

ORD record: ord-2d5e73be41e74bd6b8d5b7947fd4e529
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05856497

Reaction notes

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