Nerol → Oxiranemethanol, 3-methyl-3-(4-methyl-3-pentenyl)-
Reaction equation
[CH3:1][C:2]([CH2:6][CH:7]=[CH:8][C:9]([CH3:12])(O)[CH3:10])=[CH:3][CH2:4][OH:5].[OH:13]C/C=C(/C)\CCC=C(C)C>>[OH:5][CH2:4][CH:3]1[O:13][C:2]1([CH3:1])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:12])[CH3:10]Participants
3
Procedure
Ohloff prepared the intermediate 3,7-dimethyl-octa-2,5-dien-1,7-diol from nerol by its photosensitized air oxidation followed by reduction and cyclisation with an acid to obtain racemic nerol oxide [G. Ohloff, K. H. Schulte-Elite & B. Willhalm Helv. Chim. Acta. 47, 602, 1964]. In another publication nerol was first subjected to epoxidation at C6–C7 double bond and the epoxy derivative so obtained was heated in dimethyl amine at 150° to give 3,7-dimethyl-6-dimethyl amino-2-octen-1,7-diol which on oxidation with hydrogen peroxide and pyrolysis at 180° C. gave a diol intermediate that on acid catalysed cyclisation led to the formation of nerol oxide [G. Ohloff & B. Lienhard Helv. Chim. Acta. 48, 182, 1965].
Sources & evidence
- ORD record
- ord-ceb88aef8f754c27ae1c265ce814e2ee
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07166728B2
Reaction notes
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