Chloromethyl Methyl Ether → 1,3-bis(methoxymethoxy)benzaldehyde

HRID 1854657Notes

Reaction equation

HRID 1854657 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=[O:5].C(N(CC)C(C)C)(C)C.[CH3:20][O:21][CH2:22]Cl.[C:24]([O:27][CH2:28]C)(=O)C>ClCCl.CN(C)C1C=CN=CC=1.Cl>[CH3:20][O:21][CH2:22][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:24][O:27][CH3:28])[C:3]=1[CH:4]=[O:5]

Participants

8

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 102858012,6-Dihydroxybenzaldehyde

Product 1

HCID 117908851,3-bis(methoxymethoxy)benzaldehydeYield 79%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2,6-Dihydroxybenzaldehyde (75 mg, 0.54 mmol) was placed in a 20 mL reaction vessel, and dissolved in 1.6 mL of dry dichloromethane. To the solution were added N,N-diisopropylethylamine (0.30 mL, 1.7 mmol), 4-dimethylaminopyridine (4 mg, 0.03 mmol), and chloromethyl methyl ether (103 μL, 0.68 mmol). After being stirred at room temperature overnight, the reaction mixture was diluted with 25 mL of ethyl acetate and 5 mL of 1N HCl, and extracted. The extract 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 pale yellow oil (96.9 mg, 79%).

Workup

  1. extractionextracted
  2. washThe extract 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-832f13be32294df28ba5e04cd428405b
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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