Chloromethyl Methyl Ether → HCID 22930064, compound

HRID 1296020Notes

Reaction equation

HRID 1296020 reaction equation
[CH3:1][O:2][CH2:3]Cl.[Br:5][C:6]1[CH:7]=[C:8]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:9]([OH:14])=[C:10]([CH:13]=1)[CH:11]=[O:12]>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:9]([O:14][CH2:1][O:2][CH3:3])=[C:10]([CH:13]=1)[CH:11]=[O:12]

Participants

4

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 7970065-bromo-3-tert-butyl-2-hydroxybenzaldehyde

Product 1

HCID 22930064HCID 22930064, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

I-PrNEt2 (834 g, 6.46 g) and chloromethyl methyl ether (451 g, 5.60 mol) were gradually added to a solution of the 5-bromo-3-(tert-butyl)-2-hydroxybenzaldehyde (1333 g, 4.67 mol) in methylene chloride (4000 ml) while cooling on ice, and the mixture was stirred at room temperature for 2 days. After first distilling off the solvent under reduced pressure, ethyl acetate was added to the residue, washing was performed twice with brine, the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1338 g) as a light yellow oil.

Workup

  1. temperaturewhile cooling on ice
  2. distillationAfter first distilling off the solvent under reduced pressure, ethyl acetate
  3. additionwas added to the residue
  4. washwashing
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-ff49914c94124ab9bcd90f1630e5bf3f
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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