Toluene → Ethyl 2-[4-(2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetate

HRID 749621Notes

Reaction equation

HRID 749621 reaction equation
[I-].[Na+].Cl[Si](C)(C)C.O[CH:9]([C:15]1[C:27]([CH3:28])=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:17]([CH3:29])[CH:16]=1)[CH:10]([O:13][CH3:14])[O:11][CH3:12].C1(C)C=CC=CC=1>C(#N)C.N1C=CC=CC=1>[CH3:12][O:11][CH:10]([O:13][CH3:14])[CH2:9][C:15]1[C:27]([CH3:28])=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:17]([CH3:29])[CH:16]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 10470761Ethyl 2-[4-(1-hydroxy-2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetate

Product 1

HCID 9971795Ethyl 2-[4-(2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetateYield 90.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a stirred suspension of sodium iodide (72 g) and chlorotrimethylsilane (52 g) in acetonitrile (180 g) was added dropwise a solution of ethyl 2-[4-(1-hydroxy-2,2-dimethoxy-ethyl)-2,5-dimethylphenoxy]acetate (50 g) in acetonitrile (80 g) in an ice-salt bath. The mixture was stirred for 30 minutes, and then toluene (400 g) and pyridine (25 g) were added. The reaction mixture was washed with an aqueous solution of sodium thiosulfate, an aqueous solution of citric acid, an aqueous solution of sodium bicarbonate and brine successively. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give ethyl 2-[4-(2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetate (43 g).

Workup

  1. washThe reaction mixture was washed with an aqueous solution of sodium thiosulfate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e014dce0eb243189ab4d7868b96d24c
Source dataset
uspto-grants-2008_07
Patent number
US07402692B2

Reaction notes

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