Water → HCID 2748365, compound

HRID 1741768Notes

Reaction equation

HRID 1741768 reaction equation
[C:1]1([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[CH:17]=[CH2:18].[OH-].[Na+].O>C(O)C>[C:10]1([CH:9]([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:8])[CH2:18][CH2:17][C:16]([O:20][CH2:21][CH3:22])=[O:19])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8821Ethyl Acrylate2×HCID 99482-PhenylacetophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 2748365HCID 2748365, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 140 g (0.71 mol) of deoxybenzoin and 170 g (1.7 mol) of ethyl acrylate in 2 L of absolute ethanol at ambient temperature was added in portions 20 mL of 50% aqueous sodium hydroxide. An additional 170 g (1.7 mol) of ethyl acrylate was then added over a 15 min. period. The mixture was stirred vigorously for 2.5 h, poured into 1 L of water and extracted with 3×1 L of ether. The organic layers were combined, washed with water and brine, and dried over sodium sulfate. The filtrate was concentrated to near dryness, triturated with 1.5 L of pentane, filtered and the filtrate allowed to stand at -20° C. giving 145 g (69%) of ethyl 4,5-diphenyl-5-oxopentanoate as a white solid (top 45°-57° C.).

Workup

  1. extractionextracted with 3×1 L of ether
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationThe filtrate was concentrated
  5. customtriturated with 1.5 L of pentane
  6. filtrationfiltered
  7. customto stand at -20° C.

Sources & evidence

ORD record
ord-9ef9e1bacaeb461e8e57a68290f3c3d8
Source dataset
uspto-grants-1994_08
Patent number
US05334720

Reaction notes

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