Dimethyl Sulfoxide → (1,1'-Biphenyl)-4-carboxaldehyde

HRID 1957020Notes

Reaction equation

HRID 1957020 reaction equation
CS(C)=O.FC(F)(F)C(O)=O.[C:12]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[C:12]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:13]=[CH:14][C:15]([CH:18]=[O:19])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 19186(1,1'-Biphenyl)-4-methanol

Product 1

HCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of dimethylsulfoxide (3.9 ml, 54.4 mmol) in methylene chloride (70 ml) under nitrogen atmosphere is added trifluoroacetic acid (5.7 ml, 40.8 mmol) with stirring at -70° C. After 10 min., 4-biphenylmethanol (5 g, 27.2 mmol) is added, and after being stirred for 30 min., triethylamine (30 ml, 218 mmol) is added. The reaction mixture is allowed to warm up to r.t., diluted with water, and extracted with methylene chloride. The organic layer is washed successively with 1N hydrochloric acid and saturated sodium bicarbonate, dried over magnesium sulfate and concentrated to give 4-biphenylmethanal. To a cold solution (0° C.) of 4-biphenylmethanal in THF (50 ml) under nitrogen atmosphere is slowly added 3M phenylmagnesium bromide solution in diethyl ether (5.3 ml, 15.7 mmol) with stirring. The reaction mixture is allowed to warm up to r.t. and the stirring is continued for 15 hrs. The mixture is diluted with water and extracted with diethyl ether. The organic layer is washed with saturated ammonium chloride, dried over magnesium chloride, and concentrated in vacuo. The residue is purified by flash column chromatography on silica gel with 15% diethyl ether in hexane to give (4-biphenyl)-phenylmethanol.

Workup

  1. stirringafter being stirred for 30 min.
  2. temperatureto warm up to r.t.
  3. extractionextracted with methylene chloride
  4. washThe organic layer is washed successively with 1N hydrochloric acid and saturated sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe38361ae1764a9d9fa73018a13fa4d8
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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