Dimethylformamide → Ethyl 2-[4-(1-hydroxy-2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetate

HRID 749620Notes

Reaction equation

HRID 749620 reaction equation
CN(C)C=O.[OH:6][CH:7]([C:13]1[C:18]([CH3:19])=[CH:17][C:16]([OH:20])=[C:15]([CH3:21])[CH:14]=1)[CH:8]([O:11][CH3:12])[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(OCC)(=O)C>[OH:6][CH:7]([C:13]1[C:18]([CH3:19])=[CH:17][C:16]([O:20][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:15]([CH3:21])[CH:14]=1)[CH:8]([O:9][CH3:10])[O:11][CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 117758724-(1-Hydroxy-2,2-dimethoxyethyl)-2,5-dimethylphenol

Product 1

HCID 10470761Ethyl 2-[4-(1-hydroxy-2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetateYield 77.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To N,N-dimethylformamide (81 g) were added 4-(1-hydroxy-2,2-dimethoxyethyl)-2,5-dimethylphenol (20.0 g), potassium carbonate (15.8 g) and ethyl chloroacetate (12.4 g) at room temperature with stirring. The mixture was stirred at room temperature for an hour, and then stirred at 71° C. for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and a mixture of ethyl acetate and hexane was added to the residue. The precipitated crystals were collected by filtration to give ethyl 2-[4-(1-hydroxy-2,2-dimethoxyethyl)-2,5-dimethyl-phenoxy]acetate (21.3 g).

Workup

  1. stirringThe mixture was stirred at room temperature for an hour
  2. stirringstirred at 71° C. for 2 hours
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. additiona mixture of ethyl acetate and hexane
  7. additionwas added to the residue
  8. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-9cdf8965adf04bcb8459a74fda838810
Source dataset
uspto-grants-2008_07
Patent number
US07402692B2

Reaction notes

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