Benzene → 3,4-Dimethoxy-2-phenylacetophenone

HRID 444293

Reaction equation

HRID 444293 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5](Cl)[CH2:6][C:7]1[CH:16]=[CH:15][C:12]([O:13][CH3:14])=[C:9]([O:10][CH3:11])[CH:8]=1.[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.CC[O:27]CC>C(Cl)Cl.O>[CH3:11][O:10][C:9]1[CH:8]=[C:7]([CH:16]=[CH:15][C:12]=1[O:13][CH3:14])[CH2:6][C:5](=[O:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 5

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 30153594-(2-Chloroethyl)-1,2-dimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 123366833,4-Dimethoxy-2-phenylacetophenone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

42.8 Grams (0.32 moles) of aluminum chloride was added in portions to a solution of 45.9 g. (0.2 mole) of homoveratryl chloride and benzene (25 ml.) in methylene chloride (300 ml.). The mixture was then refluxed 1.5 hours, cooled and poured into a mixture comprised of 300 ml. of ice, 100 ml. of water and 225 ml. of concentrated hydrochloric acid. The organic phase was separated and the aqueous layer extracted with chloroform. The combined organic layers were washed with water, dried over magnesium sulfate, filtered and the solvent removed at reduced pressure to give an oil. Chromatography (2×) over alumina (ethyl acetate) followed by treatment with ether gave 3',4'-dimethoxydesoxybenzoin, m.p. 80°-81° C.

Workup

  1. temperatureThe mixture was then refluxed 1.5 hours
  2. temperaturecooled
  3. additionpoured into a mixture
  4. customThe organic phase was separated
  5. extractionthe aqueous layer extracted with chloroform
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed at reduced pressure
  10. customto give an oil

Sources & evidence

ORD record
ord-d77e4e0ce6a348a087c5f861651882f0
Source dataset
uspto-grants-1981_04
Patent number
US04263311

Linked notes

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