3-Phenylbenzaldehyde → 3-Biphenylmethanol

HRID 530495Notes

Reaction equation

HRID 530495 reaction equation
[BH4-].[Na+].[C:3]1([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[C:3]1([C:9]2[CH:10]=[C:11]([CH2:12][OH:13])[CH:14]=[CH:15][CH:16]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 1210533-PhenylbenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 6035563-BiphenylmethanolYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under nitrogen atmosphere, at 0° C., to a stirred solution of NaBH4 (0.56 g, 14.7 mmol) in dry MeOH (10 mL), 3-phenylbenzaldehyde (0.67 g, 3.68 mmol) in dry MeOH (7 mL) was added via a cannula. After 1 h, the crude was quenched with water and concentrated to dryness. The resulting oil was dissolved in AcOEt and extracted with water. The organic fraction was dried over Na2SO4, filtered and subsequently purified by column chromatography using a Teledyne ISCO apparatus, eluting with Cy/TBME (from 100:0 to 50:50) to afford the title compound (0.432 g, 64%) as a pure product. 1H NMR (CDCl3): δ 1.62-1.78 (m, 1H), 4.80 (d, J=6.0, 1H), 7.33-7.75 (m, 9H).

Workup

  1. customthe crude was quenched with water
  2. concentrationconcentrated to dryness
  3. dissolutionThe resulting oil was dissolved in AcOEt
  4. extractionextracted with water
  5. dry with materialThe organic fraction was dried over Na2SO4
  6. filtrationfiltered
  7. customsubsequently purified by column chromatography
  8. washeluting with Cy/TBME (from 100:0 to 50:50)

Sources & evidence

ORD record
ord-ffe65a14f3b447ce8a91734a9d9016fe
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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