Ammonium Chloride → [4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methanol

HRID 507915Notes

Reaction equation

HRID 507915 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[O:21])[CH:15]=2)=[C:9]([CH3:22])[CH:8]=1)[CH3:2].[BH4-].[Na+].[Cl-].[NH4+]>COCCOC.O1CCCC1>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][OH:21])[CH:15]=2)=[C:9]([CH3:22])[CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 231117224'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-carbaldehyde

Product 1

HCID 23111752[4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methanolYield 121.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

4′-(2-Ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-carbaldehyde (2.39 g, 9.70 mmol) was dissolved in a mixture of 1,2-dimethoxyethane (20 mL) and tetrahydrofuran (20 mL), sodium borohydride (0.227 g, 6.00 mmol) was added under ice-cooling, and the mixture was stirred at the same temperature for 3 hr. Aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-50% ethyl acetate/hexane) to give the title compound (3.55 g, yield 98%) as colorless crystals.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (20%-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-98fb8f4441b044dbb596e50749f0ff5b
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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