Citric Acid → HCID 72556534, compound

HRID 2238261Notes

Reaction equation

HRID 2238261 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Na+].F[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:14]2[CH:15]=[CH:16][C:17]([O:20][C:24]3[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=3)=[CH:18][CH:19]=2)[C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 687915233-(3,5-Dimethylphenyl)-2-(4-hydroxyphenyl)-acrylic acid

Product 1

HCID 72556534HCID 72556534, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 44 (2.65 g, 10 mmol) in DMF (20 mL) was added sodium hydride (60% dispersion in mineral oil, 0.88 g, 22 mmol). After gas evolution ceased 4-fluorobenzaldehyde (1.60 g, 15 mmol) was added and the reaction was stirred for 16 h. The mixture was poured over 10% citric acid (100 mL), after which a bright yellow solid formed. The solid was washed with water and then the wet solid was azeotroped and recrystallized from toluene to yield 2.97 g (80%) of a yellow solid 45.

Workup

  1. additionwas added
  2. customafter which a bright yellow solid formed
  3. washThe solid was washed with water
  4. customthe wet solid was azeotroped
  5. customrecrystallized from toluene

Sources & evidence

ORD record
ord-917f3406d3e140b29bbc1935c69acec3
Source dataset
uspto-grants-2010_05
Patent number
US07718682B2

Reaction notes

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