Chloromethyl Methyl Ether → HCID 68467344, compound

HRID 502976Notes

Reaction equation

HRID 502976 reaction equation
C(N(C(C)C)CC)(C)C.Cl[CH2:11][O:12][CH3:13].[OH:14][CH:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(Cl)Cl>[CH3:13][O:12][CH2:11][O:14][CH:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 3698303HCID 3698303, compound

Product 1

HCID 68467344HCID 68467344, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (15.9 ml) and chloro(methoxy)methane (5.48 ml) were added dropwise to a methylene chloride (270 ml) solution of ethyl 3-hydroxy-2,2-dimethyl-3-phenylpropanoate (13.5 g) under ice cooling, followed by stirring at room temperature for 3 days. After the reaction mixture was concentrated under reduced pressure, the residue was diluted with ethyl acetate and water and the organic layer washed with an aqueous hydrochloric acid solution (1M), a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution. The organic layer was subjected to evaporation under reduced pressure and then the residue was purified by silica gel column chromatography to obtain ethyl 3-(methoxymethoxy)-2,2-dimethyl-3-phenylpropanoate (13.1 g).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate and water
  3. washthe organic layer washed with an aqueous hydrochloric acid solution (1M)
  4. customThe organic layer was subjected to evaporation under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-76bd62377a8745cda8cd3787a3dc7b68
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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