Aluminum isopropoxide → 4,8-Dimethylnona-3,7-dien-2-one

HRID 347615

Reaction equation

[CH3:1][C:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[CH:3][CH:4]([OH:6])[CH3:5].C(C(=CC1C=CC=CC=1)C=O)CCCC.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>>[CH3:1][C:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[CH:3][C:4](=[O:6])[CH3:5]

Participants

Reactant 3

HCID 11143Aluminum isopropoxide

HCID 31209Amylcinnamaldehyde

HCID 1068744,8-Dimethylnona-3,7-dien-2-ol

Product 1

HCID 5496634,8-Dimethylnona-3,7-dien-2-one

Procedure

150 g of 4,8-dimethyl-3,7-nonadien-2-ol, 252.5 g alpha-amylcinnamaldehyde and 16.9 g of aluminum isopropoxide are refluxed for 30 min at 1 mbar. A product/reactant mixture is then distilled over a 15 cm packed column (reflux ratio 1:1). This gives 130 g of the mixture of E- and Z-4,8-dimethyl-3,7-nonadien-2-ol and E- and Z-4,8-dimethyl-3,7-nonadien-2-one . The sum of the two isomers of 4,8-dimethyl-3,7-nonadien-2-ol is 23%, and the sum of the two isomers of 4,8-dimethyl-3,7-nonadien-2-one is 70%.

Workup

distillationA product/reactant mixture is then distilled over a 15 cm
temperaturecolumn (reflux ratio 1:1)

Sources & evidence

ORD record: ord-a38f65812c33471aa532a5ae45ac9557
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176177B2

Linked notes

Loading…