1-(4-(1-Ethoxyethoxy)phenyl)ethyl butyrate → 1-(4-(1-Ethoxyethoxy)phenyl)ethanol

HRID 344792Notes

Reaction equation

HRID 344792 reaction equation
C([O:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]([O:18][CH2:19][CH3:20])[CH3:17])=[CH:11][CH:10]=1)[CH3:8])(=O)CCC>C(O)C.[OH-].[K+]>[CH2:19]([O:18][CH:16]([O:15][C:12]1[CH:11]=[CH:10][C:9]([CH:7]([OH:6])[CH3:8])=[CH:14][CH:13]=1)[CH3:17])[CH3:20]

Participants

4

Reactant 1

HCID 544848551-(4-(1-Ethoxyethoxy)phenyl)ethyl butyrate

Product 1

HCID 544184991-(4-(1-Ethoxyethoxy)phenyl)ethanolYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

In 210 ml of 1N ethanol solution of potassium hydroxide was dissolved 28 g (0.1 mole) of the R-form of 1-(4-(1-ethoxyethoxy)phenyl)ethyl butyrate obtained in Example 2 (i), (ii) or (iii), the mixture was reacted at room temperature over night, and the reaction mixture was concentrated under reduced pressure To the residue was added 200 ml of ether, and it was washed with 2N aqueous solution of sodium hydroxide 2 times and then with water 3 times. The resulting ether layer was dried with anhydrous magnesium sulfate and ether was distilled under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane=1/4) to give 18.9 g of R-form of 1-(4-(1-ethoxyethyoxy)phenyl)ethanol (yield: 90%).

Workup

  1. customthe mixture was reacted at room temperature over night
  2. concentrationthe reaction mixture was concentrated under reduced pressure To the residue
  3. additionwas added 200 ml of ether, and it
  4. washwas washed with 2N aqueous solution of sodium hydroxide 2 times
  5. dry with materialThe resulting ether layer was dried with anhydrous magnesium sulfate and ether
  6. distillationwas distilled under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane=1/4)

Sources & evidence

ORD record
ord-025c720f50414656a12d46e08c818d85
Source dataset
uspto-grants-1991_10
Patent number
US05053507

Reaction notes

Loading…