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

HRID 746842Notes

Reaction equation

HRID 746842 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-30bba229c16f49a5bb5ce241a6f300ae
Source dataset
uspto-grants-2008_07
Patent number
US07393968B2

Reaction notes

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