Dichloromethane → 4-Chloro-2-(methoxymethyl)-1-nitrobenzene

HRID 1910751Notes

Reaction equation

HRID 1910751 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N+:12]([O-:14])=[O:13])=[C:8]([CH2:10][OH:11])[CH:9]=1.Cl[CH2:16]Cl>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.S(OC)(OC)(=O)=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N+:12]([O-:14])=[O:13])=[C:8]([CH2:10][O:11][CH3:16])[CH:9]=1

Participants

7

Reactant 3

HCID 6344Dichloromethane2×HCID 14798Sodium HydroxideHCID 5560665-Chloro-2-nitrobenzyl alcohol

Product 1

HCID 133378004-Chloro-2-(methoxymethyl)-1-nitrobenzeneYield 72%

Reagents, catalysts & solvents 3

HCID 6497Dimethyl SulfateCatalystHCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

Sodium hydroxide (1.88 g, 44.0 mmol) in water (15 mL) was added to a solution of (5-chloro-2-nitro-phenyl)-methanol (1.1 g, 5.88 mmol) in dichloromethane (15 mL) and stirred for 10 min. Dimethyl sulfate (1.12 mL, 11.8 nmol) and tetrabutylammonium hydrogen sulfate (100 mg) were added and the mixture stirred vigorously for 8 h at room temperature. The reaction mixture was diluted with dichloromethane and the organic layer separated, washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give the crude compound. Purification by column chromatography over silica gel (100-200 mesh) using 2% ethyl acetate in petroleum ether as eluent afforded 4-chloro-2-methoxymethyl-1-nitro-benzene (850 mg, 72%) as a pale yellow liquid.

Workup

  1. stirringthe mixture stirred vigorously for 8 h at room temperature
  2. customthe organic layer separated
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give the crude compound
  8. customPurification by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-0652bc45510d46f7850dd929acca8061
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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