Hydrochloric Acid → (2,5-Dimethoxy-4-methylphenyl)-7,7-dimethyloctan-1-one

HRID 844427

Reaction equation

[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=O.C(Cl)(=O)C(Cl)=O.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[CH3:29].[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl.CN(C=O)C>[CH3:28][O:27][C:24]1[CH:23]=[C:22]([CH3:29])[C:21]([O:20][CH3:19])=[CH:26][C:25]=1[C:8](=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([CH3:1])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

1 g of 7,7-dimethyloctanoic acid is dissolved in 20 ml of DCM cooled to 0° C., 0.57 ml of oxalyl chloride is added and the mixture is then left stirring for 1 hour at 0° C. and for 2 hours at RT. 0.93 ml of 2,5-dimethoxytoluene and one drop of DMF are added, the mixture is cooled to 0° C., 940 mg of AlCl3 are then added and the mixture is left stirring for 1 hour at 0° C. and overnight at RT. It is poured into 10% HCl solution and extracted with ether, and the combined organic phases are then washed with 2N sodium hydroxide, dried and concentrated. The residue is chromatographed on silica, eluting with DCM/pentane (85/15; v/v) to give 1.05 g of the expected compound.

Workup

waitthe mixture is then left
temperaturethe mixture is cooled to 0° C.
waitthe mixture is left
stirringstirring for 1 hour at 0° C. and overnight at RT
extractionextracted with ether
washthe combined organic phases are then washed with 2N sodium hydroxide
customdried
concentrationconcentrated
customThe residue is chromatographed on silica
washeluting with DCM/pentane (85/15; v/v)

Sources & evidence

ORD record: ord-60fc8cae1c7841cdb0b8184243239d20
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380230B1

Linked notes

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