Ethyl Acetate → HCID 20800737, compound

HRID 1071608Notes

Reaction equation

HRID 1071608 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:11](OCC)(=[O:13])[CH3:12]>CN(C)C=O.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:12][CH:11]=[O:13]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 97433-FluorophenolHCID 24758Sodium hydride

Product 1

HCID 20800737HCID 20800737, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

2.00 g (17.8 mmol) of m-fluorophenol was dissolved in 50 ml of dimethylformamide, 785 mg (19.6 mmol, 60% by weight, mineral) of sodium hydride and 3.21 ml (21.3 mmol) of bromoacetaldehydediethylacetal were successively added thereto, and the mixture was heated to 60° C. After completion of the reaction, brine was added thereto and the mixture was extractedwith ethyl acetate. Theorganiclayerwaswashedwith brine, dried over magnesium sulfate and then evaporated, to give a crude product. The crude product was subjected to 105 g of Cromatorex NH silica gel (ethyl acetate:hexane=1:40), to give 3.17 g (13.9 mmol, 78.1%) of the title compound as a yellow oil.

Workup

  1. additionwas added
  2. dry with materialTheorganiclayerwaswashedwith brine, dried over magnesium sulfate
  3. customevaporated
  4. customto give a crude product

Sources & evidence

ORD record
ord-ebe75112225d4ec6bf69a08633de6d1e
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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