Hydrochloric Acid → Ethyl 3-hydroxy-3-(4-acetoxyphenyl)propionate

HRID 481798

Reaction equation

HRID 481798 reaction equation
[C:1]([O:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].N.B.Cl>CCOCC>[OH:10][CH:9]([C:8]1[CH:7]=[CH:6][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:18][CH:17]=1)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 419330Ammonia;boraneHCID 23282454Ethyl 3-(4-acetoxyphenyl)-3-oxopropanoate

Product 1

HCID 15890183Ethyl 3-hydroxy-3-(4-acetoxyphenyl)propionateYield 57.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 250 ml round bottom flask was charged with 11.25 grams (0.045 mol.) of ethyl 4-acetoxy-benzoylacetate and 150 ml of diethyl ether. The solution was stirred and ammonia-borane (1.39 gm., 0.045 mol., Alfa) was added in 4 portions. After being stirred 90 minutes at room temperature 50 ml of ether were added and the reaction mixture was slowly poured into a 400 ml beaker containing 20 ml of 3N HCl and 100 ml of crushed ice. After 15 minutes the organic phase was separated. The aqueous phase was extracted with ether (2×100 ml). The combined organic phase was washed with brine, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography, using a 7 cm. diameter column of 250 grams silica gel, packed and eluted with 25% ethyl acetate/petroleum ether. 6.53 grams of ethyl 3-hydroxy-3-(4-acetoxyphenyl)propionate was obtained. The product was identical to that obtained by method A as determined by NMR and elemental analysis.

Workup

  1. additionwere added
  2. additionthe reaction mixture was slowly poured into a 400 ml beaker
  3. customAfter 15 minutes the organic phase was separated
  4. extractionThe aqueous phase was extracted with ether (2×100 ml)
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash chromatography
  10. washeluted with 25% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-871566d7b782441b8af89109ebf63a1d
Source dataset
uspto-grants-1998_08
Patent number
US05789608

Linked notes

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