Chloromethyl Methyl Ether → 1-Chloro-3-(methoxymethoxy)benzene

HRID 1753963Notes

Reaction equation

HRID 1753963 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.Cl[CH2:19][O:20][CH3:21]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:19][O:20][CH3:21])[CH:3]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 79333-ChlorophenolHCID 81531Diisopropylethylamine

Product 1

HCID 121796641-Chloro-3-(methoxymethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 3-chlorophenol (50 g, 390.62 mmol, 1.00 equiv) in DCM (500 mL) was added DIEA (554 g, 4.29 mol, 11.00 equiv), followed by chloro(methoxy)methane (380 g, 10.00 equiv) at 20° C. The resulting mixture was allowed to react, with stirring, for 4 h at 20° C. The reaction mixture was then quenched with water. The separated organic phase was washed with water (2×), dried over Na2SO4 and then concentrated under vacuum to give 1-chloro-3-(methoxymethoxy)benzene as a white oil.

Workup

  1. customto react
  2. customThe reaction mixture was then quenched with water
  3. washThe separated organic phase was washed with water (2×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8c14796f2ada444dbeed6e86249d55e4
Source dataset
uspto-grants-2015_10
Patent number
US09168248B2

Reaction notes

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