Sodium Hydroxide → (2-Fluorobiphenyl-4-yl)methanol

HRID 1907914Notes

Reaction equation

HRID 1907914 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH4-].[Na+].[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27590832-Fluorobiphenyl-4-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 46314883(2-Fluorobiphenyl-4-yl)methanolYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Fluoro-biphenyl-4-carbaldehyde (1 gm, 5 mmole), NaBH4 were dissolved in ethanol stirred for 2 hrs, NaOH 10% was added, ethanol was evaporated, the reaction mixture was extracted with ethyl acetate, the ethyl acetate extract was dried with Na2SO4 and evaporated to produce white solid (0.8 gm, 80%). H1-NMR INOVA-500 (CDCl3) δ 2.266(s, 1H), 4.683(s, 2H), 7.142-7.168(m, 2H), 7.339-7.442(m, 4H), 7.519-7.535(m, 2H).

Workup

  1. customethanol was evaporated
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. extractionthe ethyl acetate extract
  4. dry with materialwas dried with Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-c3bd107a9e634949a272d01aafa3610d
Source dataset
uspto-grants-2013_12
Patent number
US08598169B2

Reaction notes

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