Anisole → (4-Methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone

HRID 1647310Notes

Reaction equation

HRID 1647310 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:18][CH3:19])[C:15]=1[O:16][CH3:17])[C:10](Cl)=[O:11].[C:20]1([O:26][CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:18][CH3:19])[C:15]=1[O:16][CH3:17])[C:10]([C:23]1[CH:24]=[CH:25][C:20]([O:26][CH3:27])=[CH:21][CH:22]=1)=[O:11]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 368149(4-Methoxyphenyl)(3,4,5-trimethoxyphenyl)methanoneYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous AlCl3 (260 mg, 2 mmol) was added to a well-stirred solution of 3,4,5-trimethoxybenzoyl chloride (25) (461 mg, 2 mmol) and anisole (216 mg, 2 mmol) at 0° C. in CH2Cl2 (25 mL). The mixture was stirred while allowing it to warm to room temperature. After 6 h, the resultant dark reaction mixture was poured into ice cold 5% HCl (20 mL), and the CH2Cl2 layer was separated. The aqueous layer was extracted with an additional 30 mL of CH2Cl2, and the combined CH2Cl2 solutions were washed with saturated sodium bicarbonate solution. Evaporation of solvents from the dried CH2Cl2 extract and purification of the residue by chromatography on a column of silica gel, using 5% EtOAc in hexane as eluent, gave product 27 (487 mg, 80%); mp 72°-73° C.; 1H NMR (CDCl3, 200 MHz) δ7.83 (d, J=8.7 Hz, 2H), 7.03 (s, 2H), 6.98 (d, J=8.7 Hz, 2H), 3.94 (s, 3H), 3.90 (s, 3H), 3.88 (s, 6H); CIMS (isobutane) m/e 303 (MH+, 100). Anal. (C17H18O5), C, H.

Workup

  1. customthe resultant dark reaction mixture
  2. customthe CH2Cl2 layer was separated
  3. extractionThe aqueous layer was extracted with an additional 30 mL of CH2Cl2
  4. washthe combined CH2Cl2 solutions were washed with saturated sodium bicarbonate solution
  5. customEvaporation of solvents from the dried CH2Cl2
  6. extractionextract
  7. custompurification of the residue by chromatography on a column of silica gel

Sources & evidence

ORD record
ord-dc5701759a464d72bec3d341e72304ff
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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