Water → 2-Ethyl-[1,1'-biphenyl]-3-methanol

HRID 485553Notes

Reaction equation

HRID 485553 reaction equation
[CH2:1]([C:3]1[C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].O>O1CCCC1.C(Cl)Cl>[CH2:1]([C:3]1[C:8]([CH2:9][OH:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 202706372-Ethyl-[1,1'-biphenyl]-3-carboxylic acid

Product 1

HCID 202706032-Ethyl-[1,1'-biphenyl]-3-methanolYield 106.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-ethyl-[1,1'-biphenyl]-3-carboxylic acid (2.1 g, 0.0093 mole) in 50 ml of tetrahydrofuran was added dropwise borane-tetrahydrofuran complex (1.6 g, 0.0186 mole). The reaction mixture was stirred at room temperature for approximately 18 hours. Water (6 ml) was slowly added to the reaction mixture and the solvent removed under reduced pressure to give a residue. The residue was dissolved in methylene chloride; the solution was washed with 1N aqueous sodium hydroxide, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure to give 2-ethyl-[1,1'-biphenyl]-3-methanol (2.1 g) as an oil. The ir and nmr spectra were consistent with the named compound.

Workup

  1. customthe solvent removed under reduced pressure
  2. customto give a residue
  3. washthe solution was washed with 1N aqueous sodium hydroxide
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2660d9d3e4824cb9ac094d345bcd29eb
Source dataset
uspto-grants-1985_08
Patent number
US04536591

Reaction notes

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