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

HRID 556098Notes

Reaction equation

HRID 556098 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl.[Al+3].[Cl-].[Cl-].[Cl-]>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 7519AnisoleHCID 67340Hexanoyl chloride

Product 1

HCID 808091-(4-Methoxyphenyl)hexan-1-oneYield 66.2%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A procedure similar to step 2 of Example 52 was used. n-Caproyl chloride prepared in the step 1 and methylphenyl ether were used as starting materials, allowed to react in dichloromethane in the presence of AlCl3 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 petroleum ether and ethyl acetate at a ratio of 20:1 to obtain a product as a waxy solid in a yield of 66.2%, mp: 39-40 └. 1H-NMR (CDCl3, 400 MHz) δ: 0.91 (3H, t, J=7.20 Hz, CH3), 1.30˜1.42 (4H, m, CH2CH2), 1.73 (2H, t, J=7.20 Hz, COCH2CH2), 2.91 (2H, t, J=7.20 Hz, COCH2CH2), 3.87 (3H, s, OCH3), 6.93 (2H, d, J=8.80 Hz, ArH), 7.96 (2H, d, J=8.80 Hz, ArH); ESI-MS m/e (%): 206.1 (M, 5), 163.0 (6), 150.0 (58), 135.0 (100).

Workup

  1. waitat room temperature for 3 hours

Sources & evidence

ORD record
ord-8b16528c8032409daa1965759c7f9beb
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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