Hydrochloric Acid → HCID 90411281, compound

HRID 1406834Notes

Reaction equation

HRID 1406834 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:7]=[C:6]([F:19])[C:3]=1[CH:4]=[O:5].O.[BH4-].[Na+].Cl>C(O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:7]=[C:6]([F:19])[C:3]=1[CH2:4][OH:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 225613733,5-Difluoro-4'-propyl[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 90411281HCID 90411281, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Then, 50.01 g of 2,6-difluoro-4-(4-propylphenyl)benzaldehyde and 7 mL g of water were dissolved in 35 mL of ethanol, the resultant solution was cooled with ice, and 2.18 g of sodium tetrahydroborate was slowly added to the solution. After stirring at room temperature for 2 hours, 10% hydrochloric acid was added until the reaction system became acidic, followed by stirring for 1 hour. Then, toluene was added to separate an organic layer, an aqueous layer was subjected to extraction with toluene, and the toluene extract was combined with the organic layer. The resultant mixture was washed with saturated brine and dried by adding sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was recrystallized from ethanol to yield 48.02 g of 2,6-difluoro-4-(4-propylphenyl)benzyl alcohol.

Workup

  1. additionwas slowly added to the solution
  2. stirringby stirring for 1 hour
  3. customto separate an organic layer
  4. extractionan aqueous layer was subjected to extraction with toluene
  5. extractionthe toluene extract
  6. washThe resultant mixture was washed with saturated brine
  7. customdried
  8. additionby adding sodium sulfate
  9. distillationThen, the solvent was distilled off under reduced pressure
  10. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-52af4a4311584e38bb60857f88c9c81e
Source dataset
uspto-grants-2014_12
Patent number
US08916718B2

Reaction notes

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