Chloromethyl Methyl Ether → HCID 12566141, compound

HRID 1854660Notes

Reaction equation

HRID 1854660 reaction equation
[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=[O:6].C(N(CC)C(C)C)(C)C.[CH3:21][O:22][CH2:23]Cl>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[C:3]([O:11][CH2:21][O:22][CH3:23])=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=[O:6]

Participants

8

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 666603,5-DichlorosalicylaldehydeHCID 81531Diisopropylethylamine

Product 1

HCID 12566141HCID 12566141, compoundYield 85.2%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,5-Dichloro-2-hydroxy-benzaldehyde (200 mg, 1.57 mmol) was placed in a 20 mL reaction vessel, and dissolved in 4.7 mL of dry dichloromethane. To the solution were added N,N-diisopropylethylamine (0.40 mL, 2.3 mmol), 4-dimethylaminopyridine (13 mg, 0.11 mmol), and chloromethyl methyl ether (149 μL, 1.96 mmol). After being stirred at room temperature overnight, the reaction mixture was diluted with 100 mL of ethyl acetate and 20 mL of 1N HCl, and extracted. The organic layer was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a white solid (314.4 mg, 85%).

Workup

  1. extractionextracted
  2. washThe organic layer was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-57aca8456a4b4975b9df427ef60ac819
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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