Chloromethyl Methyl Ether → HCID 81589004, compound

HRID 1942477Notes

Reaction equation

HRID 1942477 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[CH3:13][O:14][CH2:15]Cl.[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][O:14][CH3:15])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 3871792-Bromo-5-hydroxybenzaldehyde

Product 1

HCID 81589004HCID 81589004, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-5-hydroxybenzaldehyde (4.4 g) in tetrahydrofuran (100 ml) were added sodium hydride (1.2 g) and chloromethyl methyl ether (2.1 ml), and the mixture was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.84 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-40b5b3192caa499183327d6f78678376
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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