1,2-Dimethoxyethane → 4-Hydroxy-(1,1'-biphenyl)-3-carbaldehyde

HRID 1514007Notes

Reaction equation

HRID 1514007 reaction equation
Br[C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH:7]([C:6]1[CH:9]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=[CH:4][C:5]=1[OH:10])=[O:8]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 728635-Bromosalicylaldehyde

Product 1

HCID 122646584-Hydroxy-(1,1'-biphenyl)-3-carbaldehydeYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In an atmosphere of argon, 496 g (2.46 mol) of 5-bromosalicylaldehyde, 361 g (2.96 mol) of phenylboronic acid, 57 g (49.0 mmol) of tetraxis(triphenylphosphine)palladium(0), 8.6 L of DME and 784 g of sodium carbonate/3.7 L of water were charged, and subjected to heating under reflux with stirring for 17 hours. After cooling the resultant to room temperature, 3 L of toluene was added, and then an aqueous layer was removed. An organic layer was washed with water, and dried with magnesium sulfate. The solvent was distilled off under a reduced pressure. The crystals were purified by silica gel chromatography, whereby 382 g of 3-formyl-4-hydroxybiphenyl was obtained (yield: 78%).

Workup

  1. temperatureto heating
  2. temperatureunder reflux
  3. customan aqueous layer was removed
  4. washAn organic layer was washed with water
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off under a reduced pressure
  7. customThe crystals were purified by silica gel chromatography

Sources & evidence

ORD record
ord-2177e73fe4ce40178b81097a8b81cb95
Source dataset
uspto-grants-2012_07
Patent number
US08221907B2

Reaction notes

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