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

HRID 3682

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 for reacting them together. To the reaction solution was added ethyl acetate (300 ml), and the resulting solution was washed in dilute hydrochloric acid, in water, and in a 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 a 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-b4abd6c40e154847ac62183456b57efd
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05734067

Linked notes

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