Benzyl Alcohol → Ethyl 4-(benzyloxy)-3-oxobutanoate

HRID 1397073Notes

Reaction equation

HRID 1397073 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:12][C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>C(OCC)C.O>[CH2:1]([O:8][CH2:12][C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 9813448Ethyl 4-(benzyloxy)-3-oxobutanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Benzyl alcohol (19.7 g, 182.3 mmol) was slowly added to a suspension of sodium hydride (15.9 g 55% in mineral oil, 364.5 mmol) in anhydrous diethyl ether (116 mL) and the resulting mixture was stirred at room temperature for 1 hour. It was then diluted with some diethyl ether to ensure good stirring. Ethyl 4-chloro-3-oxobutanoate (12.3 mL, 91.1 mmol) was then slowly added and the mixture was stirred at room temperature overnight. The reaction mixture was cooled with an ice bath and then diluted with cold water and diethyl ether pH was adjusted to 4 with 5 N HCl and it was extracted three times with diethyl ether containing some ethyl acetate. The combined organic phases were dried over Na2SO4 and it was concentrated to dryness, thus obtaining the title compound with quantitative yield as a crude product that was used as such in the following step.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. temperatureThe reaction mixture was cooled with an ice bath
  3. extractionwas extracted three times with diethyl ether containing some ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4 and it
  5. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-d84e04118b734c069955a40c94fe3935
Source dataset
uspto-grants-2014_12
Patent number
US08901146B2

Reaction notes

Loading…