HCID 13894227, compound → beta-Damascenone

HRID 1633178Notes

Reaction equation

HRID 1633178 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[C:10]([OH:17])(CC=C)[CH2:11][CH:12]=[CH2:13].CC(C)([O-])C.[K+]>CN(C=O)C>[CH3:13]/[CH:12]=[CH:11]/[C:10]([C:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:17]

Participants

4

Reactant 2

HCID 13894227HCID 13894227, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 5366074beta-DamascenoneYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11.6 g (0.05M) of 2,6,6-trimethyl-1-[4-hydroxy-hepta-1,6-dien-4-yl]-cyclohexa-1,3-diene were treated as indicated in the preceding example with 8.6 g (0.075M) of potassium tert-butoxide in 50 ml of DMF. β-Damascenone was obtained in 80% yield (7.1 g).

Sources & evidence

ORD record
ord-ba3422abe8274cb5939961888eb8dd83
Source dataset
uspto-grants-1984_10
Patent number
US04479011

Reaction notes

Loading…