Anisole → 1-(4-Methoxy-phenyl)-3-(4-nitro-phenyl)-propan-1-one

HRID 556036Notes

Reaction equation

HRID 556036 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](Cl)=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Al+3].[Cl-].[Cl-].[Cl-]>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:12](=[O:13])[CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 147973603-(4-Nitrophenyl)propionyl chloride

Product 1

HCID 665542091-(4-Methoxy-phenyl)-3-(4-nitro-phenyl)-propan-1-oneYield 81.3%

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Procedure

A procedure similar to step 2 of Example 1 was used, the 3-(4-nitro-phenyl)-propionyl chloride prepared in the step 2 and methylphenyl ether were used as starting materials, and anhydrous AlCl3 was used as catalyst, the obtained product was white solid in a yield of 81.3%, mp: 123-125 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.18 (2H, t, J=7.00 Hz), 3.30 (2H, t, J=7.00 Hz), 3.87 (3H, s, OCH3), 6.93 (2H, d, J=8.96 Hz, ArH), 7.42 (2H, d, J=8.60 Hz, ArH), 7.93 (2H, d, J=8.96 Hz, ArH), 8.15 (2H, d, J=8.60 Hz, ArH); EI-MS m/e (%): 285.0 (M+, 62), 134 (100).

Sources & evidence

ORD record
ord-dee63e4f4aaf4fa6b27dd934c1c98e5a
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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