Chloromethyl Methyl Ether → 1,2-Dimethoxy-4-(methoxymethoxy)benzene

HRID 63269Notes

Reaction equation

HRID 63269 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CCN(C(C)C)C(C)C.[CH3:21][O:22][CH2:23]Cl>C(Cl)Cl>[CH3:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([O:11][CH2:21][O:22][CH3:23])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 162513,4-DimethoxyphenolHCID 81531Diisopropylethylamine

Product 1

HCID 149105661,2-Dimethoxy-4-(methoxymethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3,4-bis(methyloxy)phenol (Commercial eg Alfa Aesar) (1.0 g) and DIPEA (2.28 ml) in DCM (15 ml) was added chloromethyl methyl ether (0.74 ml) at 0 C. After stirring at 25-30 C. for 17 h, the reaction was washed with dilute hydrochloric acid and saturated aqueous sodium bicarbonate. This was dried over sodium sulphate and purified through silica eluting with 0-5% ethyl acetate in hexane, to give the title compound, 0.80 g

Workup

  1. washthe reaction was washed with dilute hydrochloric acid and saturated aqueous sodium bicarbonate
  2. dry with materialThis was dried over sodium sulphate
  3. custompurified through silica eluting with 0-5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4b50b033a95a448ea8fd081aada03c0c
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Reaction notes

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