Sodium Hydroxide → HCID 57626302, compound

HRID 2077268Notes

Reaction equation

HRID 2077268 reaction equation
[CH2:1]([C:3]1[C:4]([F:11])=[C:5]([CH:8]=[CH:9][CH:10]=1)C=O)[CH3:2].C([C:14](=[O:18])[C:15]([O-:17])=[O:16])C.[OH-].[Na+]>C(O)C>[O:18]=[C:14](/[CH:2]=[CH:1]/[C:3]1[CH:10]=[CH:9][CH:8]=[CH:5][C:4]=1[F:11])[C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 35932772-KetobutyrateHCID 19896207HCID 19896207, compound

Product 1

HCID 57626302HCID 57626302, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a magnetically stirred solution of ethyl 2-fluorobenzaldehyde (11.7 ml, 110 mmol) and ethylglyoxalate (11.1 ml, 100 mmol) in ethanol (50 ml) was slowly added a solution of sodium hydroxide (4.4 g (110 mmol) in 50 ml water) in a nitrogen atmosphere while the temperature was kept between 0° C. and 10° C. After stirring for another 45 minutes the reaction mixture was allowed to attain room temperature and stirred for 2 hours. The formed precipitate was collected by filtration and successively washed with ethanol and a 1N HCl solution (200 ml) and subsequently dried to give E-2-oxo-4-(2-fluorophenyl)-but-3-enoic acid (11.1 gram, 57% yield) Melting point: 100-102.5° C. 1H-NMR (400 MHz, CDCl3) δ 7.13-7.27 (m, 2H), 7.45-7.53 (m, 1H) 7.66-7.74 (m, 2H), 8.26 (d, J=16, 1H), invisible —OH proton.

Workup

  1. customwas kept between 0° C. and 10° C
  2. customto attain room temperature
  3. stirringstirred for 2 hours
  4. filtrationThe formed precipitate was collected by filtration
  5. washsuccessively washed with ethanol
  6. dry with materiala 1N HCl solution (200 ml) and subsequently dried

Sources & evidence

ORD record
ord-3daa6e479312492881b8c3ed4b30fd41
Source dataset
uspto-grants-2011_04
Patent number
US07928134B2

Reaction notes

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