Dimethyl Sulfate → 569328-82-1

HRID 37830Notes

Reaction equation

HRID 37830 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.S(OC)(O[CH3:19])(=O)=O>O.ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N+:12]([O-:14])=[O:13])=[C:8]([CH2:10][O:11][CH3:19])[CH:9]=1

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 5560665-Chloro-2-nitrobenzyl alcohol

Product 1

HCID 13337800569328-82-1Yield 72%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

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 mmol) 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 phase was 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 phase was 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-0b89b9f93f30457d8d6f2e738207f43b
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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