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

HRID 1757947Notes

Reaction equation

HRID 1757947 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+].[CH3:33]COCC>C1COCC1>[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

7

Reactant 5

HCID 3283Diethyl Ether2×HCID 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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Methyl-(1,1'-biphenyl)-4-carboxylic acid, methyl ester (1.43 g) in ether (25 ml) and THF (25 ml) was added over 5 min to LiAlH4 (420 mg) in ether (25 ml). The mixture was stirred at room temperature for 1h 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 cyclohexane-methanol 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 cyclohexane-methanol

Sources & evidence

ORD record
ord-752fcdc724d043d6a8062c3409136960
Source dataset
uspto-grants-1983_02
Patent number
US04371530

Reaction notes

Loading…