1-Pentanol → 2-(2,3-Dimethoxyphenoxy)acetophenone

HRID 2299175Notes

Reaction equation

C(O)CCCC.[CH3:7][O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:17].Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25](=[O:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C>[CH3:7][O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH2:26][C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:19]=1)=[O:27]

Participants

Conditions

Temperature: 150 °C

Procedure

Amyl alcohol (44 ml) was added to 2,3-dimethoxyphenol (5 g), 2′-bromoacetophenone (7 g), potassium carbonate (6.7 g) and copper acetate (1.1 g), followed by heating and stirring at 150° C. for 8 hours. To the reaction solution was added ethyl acetate (300 ml), and the resulting solution was washed in dilute hydrochloric acid, in water, and in an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvents therein were distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent:hexane:ethyl acetate=8:1), to recover 2-(2,3-dimethoxyphenoxy)acetophenone (7.6 g; yield of 87%). By 1H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

Workup

temperatureby heating
washthe resulting solution was washed in dilute hydrochloric acid, in water
dry with materialin an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
distillationthe solvents therein were distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (developing solvent:hexane:ethyl acetate=8:1)

Sources & evidence

ORD record: ord-9e1faf37b9df4269b548be75a89505bb
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495592B1

Reaction notes

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