Acetic Acid → Ethyl 4-(benzyloxy)-3-oxobutanoate

HRID 274100Notes

Reaction equation

HRID 274100 reaction equation
[H-].[Na+].C1COCC1.Cl[CH2:9][C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(O)(=O)C.[CH2:22]([OH:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:22]([O:29][CH2:9][C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 244Benzyl Alcohol2×HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

80 g of 60% NaH are added in portions to 800 ml of anhydrous THF. The medium is cooled to 10° C. and maintained at this temperature. 500 ml of benzyl alcohol are then introduced dropwise. A solution of 65.8 g of ethyl 4-chloroacetoacetate in 200 ml of benzyl alcohol is then added. The mixture is stirred at room temperature for 20 h. It is neutralized by the slow addition of acetic acid (120 ml) while being cooled with an ice bath. The whole is then poured into a mixture of water and ice and extracted with ether. The organic phase is washed with a solution of sodium bicarbonate, dried over MgSO4 and then concentrated to give an orange oil. The product is purified by two successive distillations to give a yellow oil.

Workup

  1. temperaturemaintained at this temperature
  2. temperaturewhile being cooled with an ice bath
  3. extractionextracted with ether
  4. washThe organic phase is washed with a solution of sodium bicarbonate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give an orange oil
  8. distillationThe product is purified by two successive distillations
  9. customto give a yellow oil

Sources & evidence

ORD record
ord-d9f9a6f759c5470985f41e2582993a36
Source dataset
uspto-grants-1995_02
Patent number
US05387747

Reaction notes

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