Hydrochloric Acid → 4-Methoxy-3-methylbenzophenone

HRID 1030672Notes

Reaction equation

HRID 1030672 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH3:10])[CH:3]=1.[Mg].[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>O1CCCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:19])=[CH:3][C:4]=1[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 6083154-Bromo-1-methoxy-2-methylbenzeneHCID 5462224Magnesium

Product 1

HCID 115141104-Methoxy-3-methylbenzophenoneYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The corresponding Grignard reagent was prepared from 10 g of 4-bromo-2-methylanisole and 1.21 g of magnesium shavings in 30 ml of tetrahydrofuran and was added dropwise to a solution, pre-cooled to -72°, of 7 g of benzoyl chloride in 80 ml of tetrahydrofuran. In so doing, the temperature was held at below -65°. After the dropwise addition the mixture was stirred at 20° for 0.5 hour, whereupon it was hydrolyzed with 400 ml of ice-water. The solution, acidified with dilute hydrochloric acid, was extracted with ether and the organic phase was dried and evaporated. By chromatography of the residue on silica gel with hexane:ethyl acetate 7:3) there were obtained 6.17 g (55%) of 4-methoxy-3-methylbenzophenone as a yellowish oil.

Workup

  1. additionwas added dropwise to a solution
  2. customwas held at below -65°
  3. additionAfter the dropwise addition the mixture
  4. extractionwas extracted with ether
  5. customthe organic phase was dried
  6. customevaporated

Sources & evidence

ORD record
ord-acc9ffd2ecf747eba2b74a77999c4661
Source dataset
uspto-grants-1992_04
Patent number
US05106878

Reaction notes

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