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

HRID 2121844Notes

Reaction equation

HRID 2121844 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 diethylether. 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 refluxfor6hours. 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-benzyloxyethyl)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 diethylether
  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 under refluxfor6hours
  11. 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-90d7cfba75344b19ad0127bb8db68b66
Source dataset
uspto-grants-2004_02
Patent number
US06696489B1

Reaction notes

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