Acetonitrile → Ethyl 2-[4-(2-ethoxy-2-hydroxyethyl)-2,5-dimethylphenoxy]acetate

HRID 747586Notes

Reaction equation

HRID 747586 reaction equation
C[O:2][CH:3]([O:20][CH3:21])[CH2:4][C:5]1[C:17]([CH3:18])=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]([CH3:19])[CH:6]=1.Cl(O)(=O)(=O)=O.[C:27](#N)C>>[CH2:21]([O:20][CH:3]([OH:2])[CH2:4][C:5]1[C:17]([CH3:18])=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]([CH3:19])[CH:6]=1)[CH3:27]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 24247Perchloric AcidHCID 9971795Ethyl 2-[4-(2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetate

Product 1

HCID 10108608Ethyl 2-[4-(2-ethoxy-2-hydroxyethyl)-2,5-dimethylphenoxy]acetateYield 48.8%

Procedure

Ethyl 2-[4-(2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetate (43 g) was dissolved in acetonitrile (190 g) while stirring. To the resulting solution was added 10% perchloric acid (216 g), and the mixture was stirred for an hour at room temperature. The reaction mixture was partitioned between toluene (340 g) and water (200 g). The organic layer was washed with water, an aqueous solution of sodium bicarbonate and brine successively, and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was dissolved in ethanol (180 g), and the solvent was removed under reduced pressure. The residue was dissolved with hexane (86 g) and ethanol (37 g). After seed crystals were added, the solution was stirred at 0-10° C. for 2 hours. Hexane (220 g) was added, and the resulting suspension was stirred at 0-10° C. for 2 hours. The precipitated crystals were filtered to give ethyl 2-[4-(2-ethoxy-2-hydroxyethyl)-2,5-dimethylphenoxy]acetate (21 g).

Workup

  1. stirringthe mixture was stirred for an hour at room temperature
  2. customThe reaction mixture was partitioned between toluene (340 g) and water (200 g)
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous solution of sodium bicarbonate and brine successively, and dried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. dissolutionThe residue was dissolved in ethanol (180 g)
  7. customthe solvent was removed under reduced pressure
  8. dissolutionThe residue was dissolved with hexane (86 g) and ethanol (37 g)
  9. additionAfter seed crystals were added
  10. stirringthe solution was stirred at 0-10° C. for 2 hours
  11. additionHexane (220 g) was added
  12. stirringthe resulting suspension was stirred at 0-10° C. for 2 hours
  13. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-fc1954b82f574ad5962642dc5dc7447d
Source dataset
uspto-grants-2008_07
Patent number
US07396954B2

Reaction notes

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