Chloromethyl Methyl Ether → HCID 11550252, compound

HRID 1040404Notes

Reaction equation

HRID 1040404 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(N(CC)C(C)C)(C)C.[CH3:22][O:23][CH2:24]Cl>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CCCCCC>[CH3:22][O:23][CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

8

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 81531Diisopropylethylamine

Product 1

HCID 11550252HCID 11550252, compoundYield 98%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-hydroxy-2-nitrobenzaldehyde (3.00 g, 18.0 mmol) in 36 mL of dichloromethane was added N,N-diisopropylethylamine (9.2 mL, 54 mmol), 4-dimethylaminopyridine (0.22 g, 1.8 mmol), and chloromethyl methyl ether (2.7 mL, 36 mmol) at room temperature, successively. After being stirred at room temperature overnight, the reaction mixture was diluted with a 1:1 solution (200 mL) of ethyl acetate and hexane. The solution was washed with 1M HCl four times, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo to obtain the title compound as a white solid (3.71 g, 98%).

Workup

  1. washThe solution was washed with 1M HCl four times, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7c266bcfa17845cabb28a2b0769a7656
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

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