Tetrahydrofuran → (4'-Methyl(1,1'-biphenyl)-4-yl)methanol

HRID 66569Notes

Reaction equation

HRID 66569 reaction equation
C[C:2]1([C:14]([O:16]C)=O)[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH2:33]1COCC1>>[CH3:33][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH2:14][OH:16])=[CH:7][CH:6]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86738513Methyl 4-methyl[1,1-biphenyl]-4-carboxylate

Product 1

HCID 1394290(4'-Methyl(1,1'-biphenyl)-4-yl)methanol

Procedure

4-Methyl-(1,1'-biphenyl)-4-carboxylic acid, methyl ester (1.43 g) in ER (25 ml) and THF (25 ml) was added over 5 min to LiAlH4 (420 mg) in ER (25 ml). The mixture was stirred at room temperature for 1 h and then cooled in ice. Aqueous NaOH (1 M, 2.1 ml) was added and after stirring (15 min) excess anhydrous Na2SO4 was added. The mixture was filtered and the filtrate evaporated to give a solid. Crystallisation from cyclohexanemethanol gave the title compound (1.04 g) m.p. 128°-31°.

Workup

  1. temperaturecooled in ice
  2. additionwas added
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated
  5. customto give a solid
  6. customCrystallisation from cyclohexanemethanol

Sources & evidence

ORD record
ord-a626a6da84b84a85a11131bfe8c10490
Source dataset
uspto-grants-1982_08
Patent number
US04342756

Reaction notes

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