Chloromethyl Methyl Ether → 3-Methoxy-4-methoxymethoxy-benzonitrile

HRID 1016615Notes

Reaction equation

HRID 1016615 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].C(N(C(C)C)CC)(C)C.Cl[CH2:22][O:23][CH3:24]>C(Cl)Cl>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[O:1][CH2:22][O:23][CH3:24])[C:6]#[N:7]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 781354-Hydroxy-3-methoxybenzonitrileHCID 81531Diisopropylethylamine

Product 1

HCID 222583333-Methoxy-4-methoxymethoxy-benzonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-hydroxy-3-methoxy-benzonitrile (11, 1.5 g, 10 mmol) and diisopropylethylamine (2.7 mL, 15 mmol) in CH2Cl2 (50 mL) was treated with chloromethylmethylether (0.92 mL, 12 mmol) and stirred for 3 h. After diluted with CH2Cl2, the mixture was washed with H2O, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel using EtOAc:Hex (1:2) as eluant to give 12 as white solid (1.54 g, 80%).

Workup

  1. washthe mixture was washed with H2O
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-de16a529e10344f6a3f98e7a744a07a7
Source dataset
uspto-grants-2002_11
Patent number
US06476076B1

Reaction notes

Loading…