p-Anisoyl chloride → 2,6-Dimethoxy-4-methylphenyl 4-methoxyphenyl ketone

HRID 1857132Notes

Reaction equation

HRID 1857132 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>O1CCCC1>[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([C:8]2[C:7]([O:9][CH3:10])=[CH:6][C:5]([CH3:11])=[CH:4][C:3]=2[O:2][CH3:1])=[O:19])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 778443,5-Dimethoxytoluene

Product 1

HCID 542550422,6-Dimethoxy-4-methylphenyl 4-methoxyphenyl ketoneYield 20.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,5-Dimethoxy toluene (1.00 g) obtained in Example 44 was dissolved in anhydrous tetrahydrofuran (10 ml), commercially available 2.5 M n-butyllithium-hexane solution (2.90 ml) was added at -45° C. under nitrogen, and the admixture was stirred for 3 hours. Commercially available 4-methoxybenzoyl chloride (1.23 g) was dissolved in tetrahydrofuran (10 ml), and the resulting solution was added slowly to the admixture at -45° C. The reaction mixture was stirred at room temperature for 1 hour and then partitioned between water and chloroform. The chloroform layer was dried with anhydrous magnesium sulfate, the solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (5/1) to obtain 384 mg of the title compound (yield: 20%).

Workup

  1. additioncommercially available 2.5 M n-butyllithium-hexane solution (2.90 ml) was added at -45° C. under nitrogen
  2. additionthe resulting solution was added slowly to the admixture at -45° C
  3. stirringThe reaction mixture was stirred at room temperature for 1 hour
  4. custompartitioned between water and chloroform
  5. dry with materialThe chloroform layer was dried with anhydrous magnesium sulfate
  6. customthe solvent was removed by reduced-pressure distillation
  7. customthe resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (5/1)

Sources & evidence

ORD record
ord-6b89c70bd49a43e6ab71b12271433e96
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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