Citric Acid → HCID 23111728, compound

HRID 273379Notes

Reaction equation

HRID 273379 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[O:17])[CH:11]=1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][OH:17])[CH:11]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 23111729HCID 23111729, compound

Product 1

HCID 23111728HCID 23111728, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2′,4′,6′-Trimethylbiphenyl-3-carbaldehyde (2.36 g, 10.5 mmol) was dissolved in ethanol (20 mL), and sodium borohydride (0.40 g, 10.6 mmol) was added to the solution. After stirring under ice-cooling for 3 hrs., aqueous citric acid solution was added to the reaction solution. The mixture was extracted with ethyl acetate, washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5-1:2) to give the title compound (1.66 g, yield 70%) as a colorless oil.

Workup

  1. temperaturecooling for 3 hrs
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5-1:2)

Sources & evidence

ORD record
ord-38a822c5ad494cf0b44017ae6286d3fd
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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