Acetone → Ethyl 2-[4-(2-benzyloxyethyl)phenoxy]-2-methylpropionate

HRID 1006452Notes

Reaction equation

HRID 1006452 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:18].Cl[C:20](Cl)(Cl)[C:21]([CH3:24])(O)[CH3:22].[OH-].[K+].[CH3:29][C:30](C)=[O:31]>>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:21]([CH3:24])([CH3:22])[C:20]([O:31][CH2:30][CH3:29])=[O:18])=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 122198322-Propanol, 1,1,1-trichloro-2-methyl-, hydrateHCID 154534934-(2-Benzyloxyethyl)phenol

Product 1

HCID 15453494Ethyl 2-[4-(2-benzyloxyethyl)phenoxy]-2-methylpropionate

Procedure

To a stirred solution of 4-(2-benzyloxyethyl)phenol (420 mg) and 1,1,1-trichloro-2-methyl-2-propanol hydrate (690 mg) in acetone (5 ml) was added potassium hydroxide (320 mg) three times (total 960 mg) at intervals of 10 minutes under ice-cooling, and the mixture was stirred for 16 hours at room temperature. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in ice-water and washed with diethyl ether. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. A solution of thionyl chloride (400 μl) in ethanol (10 ml) was added to the residue, and the mixture was heated under reflux for 6hours. After the reaction mixture was concentrated under reduced pressure, purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=5/1) gave ethyl 2-[4-(2-benzyloxy-ethyl)phenoxy]-2-methylpropionate (485 mg).

Workup

  1. temperaturecooling
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ice-water
  4. washwashed with diethyl ether
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. additionA solution of thionyl chloride (400 μl) in ethanol (10 ml) was added to the residue
  10. temperaturethe mixture was heated
  11. temperatureunder reflux for 6hours
  12. concentrationAfter the reaction mixture was concentrated under reduced pressure, purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=5/1)

Sources & evidence

ORD record
ord-09261d1b29e54408a0194da4ae0fec9d
Source dataset
uspto-grants-2004_09
Patent number
US06790865B2

Reaction notes

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