1,3-Dimethoxybenzene → 2-Butyl-1,3-dimethoxybenzene

HRID 1977921Notes

Reaction equation

HRID 1977921 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.I[CH2:12][CH2:13][CH2:14][CH3:15]>>[CH2:12]([C:4]1[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=1[O:9][CH3:10])[CH2:13][CH2:14][CH3:15]

Participants

3

Reactant 2

HCID 90251,3-DimethoxybenzeneHCID 10962Butyl iodide

Product 1

HCID 5248402-Butyl-1,3-dimethoxybenzeneYield 71%

Procedure

1,3-Dimethoxybenzene (15.0 g, 109 mmol) was alkylated with 1-iodobutane as described above for the preparation of Example 10(A) except that the final reaction mixture was not refluxed. Purification via silica gel chromatography (ethyl acetate/hexane) provided 15.0 g (71%) of the title intermediate product as a yellow oil: NMR (CDCl3) 7.18 (t, J=8.2 Hz, 1H), 6.59 (d, J=9.7 Hz, 2H), 3.84 (s, 6H), 2.70 (t, J=8.7 Hz, 2H), 1.50 (hextet, J=6 Hz, 2H), 1.44 (quintet, J=6 Hz, 2H), 0.98 (t, J=8.2 Hz, 3H); MS-FD m/e 194 (p).

Workup

  1. customas described above for the preparation of Example 10(A) except that the final
  2. customreaction mixture
  3. temperaturewas not refluxed
  4. customPurification via silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f533e08075dc44868fb956197ce4e891
Source dataset
uspto-grants-2001_05
Patent number
US06235785B1

Reaction notes

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