Anisole → 1-(4-Methoxyphenyl)-4-phenylbutan-1-one

HRID 556092Notes

Reaction equation

HRID 556092 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl.[Al+3].[Cl-].[Cl-].[Cl-]>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 7519AnisoleHCID 117898654-Phenylbutanoyl Chloride

Product 1

HCID 445894361-(4-Methoxyphenyl)-4-phenylbutan-1-oneYield 57.5%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A procedure similar to step 2 of 5.3.1 was used. 4-Phenylbutyryl chloride prepared in the step 1 and methylphenyl ether were used as starting materials, allowed to react in dichloromethane with AlCl3 as catalyst, stirred at −10° C. to −15° C. for 30 minutes and then at room temperature for 3 hours, a crude product was obtained, purified under a reduced pressure by silica gel column chromatography eluted with a gradient of petroleum ether and ethyl acetate at a ratio of 20:1-10:1 (V:V) to obtain a product as a white crystal in a yield of 57.5%, mp: 60-61 └. 1H-NMR (CDCl3, 400 MHz) δ: 2.07 (2H, quintuple, J=7.56 Hz), 2.72 (2H, t, J=7.56 Hz), 2.93 (2H, t, J=7.56 Hz), 3.86 (3H, s, OCH3), 6.91 (2H, d, J=7.00 Hz, ArH), 7.16˜7.21 (5H, m, ArH), 7.91 (2H, d, J=7.00 Hz, ArH); FAB-MS: 255.2 (M+1, 100), 150.1 (27), 135.1 (22), 91.1 (7).

Workup

  1. waitat room temperature for 3 hours
  2. customa crude product was obtained
  3. custompurified under a reduced pressure by silica gel column chromatography
  4. washeluted with a gradient of petroleum ether and ethyl acetate at a ratio of 20:1-10:1 (V:V)

Sources & evidence

ORD record
ord-6334f943075a40c5af90b661003f422d
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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