Chloromethyl Methyl Ether → HCID 12217529, compound

HRID 1821696Notes

Reaction equation

HRID 1821696 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl[CH2:14][O:15][CH3:16].[Cl-].[NH4+]>CN(C)C=O>[CH3:14][O:15][CH2:16][O:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5227773-Methylsalicylaldehyde

Product 1

HCID 12217529HCID 12217529, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide(50 mL) was dissolved 4.96 g (36.5 mmol) of 2-hydroxy-3-methylbenzaldehyde, 2.19 g (54.6 mmol) of 60% sodium hydride was added to the solution in an ice bath and the resulting mixture was stirred for 10 minutes. To the mixture was added 3.59 mL (47.3 mmol) of chloro(methoxy)methane in an ice bath, and the resulting mixture was stirred at room temperature for 1 hour and 30 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (Daisogel 1001W, hexane:ethyl acetate=50:1) to obtain 6.60 g (36.6 mmol, Yield: 100%) of 2-(methoxymethoxy)-3-methylbenzaldehyde.

Workup

  1. additionwas added to the solution in an ice bath
  2. stirringthe resulting mixture was stirred at room temperature for 1 hour and 30 minutes
  3. extractionextracted with ethyl acetate
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. customthe residue was purified by silica gel column chromatography (Daisogel 1001W, hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-c7627bd5b27b4e4da955ca216846d256
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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