4-Hydroxybenzaldehyde → 4-((2',6'-Dimethyl-[1,1'-biphenyl]-3-yl)methoxy)benzaldehyde

HRID 1518673Notes

Reaction equation

HRID 1518673 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][OH:16])[CH:10]=1.O[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.C1(C)C=CC=CC=1>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=2)[CH:10]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 230827203-(2,6-Dimethylphenyl)benzyl alcohol

Product 1

HCID 866915124-((2',6'-Dimethyl-[1,1'-biphenyl]-3-yl)methoxy)benzaldehydeYield 80.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2′,6′-dimethyl-[1,1′-biphenyl]-3-yl)methanol (1.0 g), 4-hydroxybenzaldehyde (0.58 g), and triphenylphosphine (1.48 g) in tetrahydrofuran (10 mL), a solution of 40% diisopropylazodicarboxylic acid diisopropyl in toluene (1.09 mL) was added under ice-cooling and the resultant reaction mixture was stirred under ice-cooling for 3 hours. A solution of diisopropyl azodicarboxylate in toluene (0.6 mL) was further added and the resultant reaction mixture was stirred at room temperature for 12 hours. From the reaction mixture, the solvent was distilled off under reduced pressure to give a residue and water was added to the resultant residue. The mixture was extracted with an organic solvent and the resultant organic phase was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent; n-heptane:ethyl acetate=100:0 to 100:20) to give the title compound (1.2 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. customthe resultant reaction mixture
  3. temperaturecooling for 3 hours
  4. customthe resultant reaction mixture
  5. stirringwas stirred at room temperature for 12 hours
  6. distillationFrom the reaction mixture, the solvent was distilled off under reduced pressure
  7. customto give a residue and water
  8. extractionThe mixture was extracted with an organic solvent
  9. dry with materialthe resultant organic phase was dried over anhydrous sodium sulfate
  10. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
  11. customthe resultant residue was purified by silica gel column chromatography (eluent; n-heptane:ethyl acetate=100:0 to 100:20)

Sources & evidence

ORD record
ord-889f8f7b170d44e4bb6a0935509dcc1f
Source dataset
uspto-grants-2015_07
Patent number
US09072758B2

Reaction notes

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