Hydrochloric Acid → 4'-Hydroxy-3-methyl[1,1'-biphenyl]-4-carbaldehyde

HRID 1180327Notes

Reaction equation

HRID 1180327 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#N)=[C:10]([CH3:16])[CH:9]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C[OH:28].Cl>C1(C)C=CC=CC=1.O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[O:28])=[C:10]([CH3:16])[CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 136359914'-Hydroxy-3-methyl-1,1'-biphenyl-4-carbonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 589785354'-Hydroxy-3-methyl[1,1'-biphenyl]-4-carbaldehydeYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 4′-hydroxy-3-methyl[1,1′-biphenyl]-4-carbonitrile (500 mg, 2.39 mmol) in dry toluene was cooled to −78° C. and diisobutylaluminum hydride (4.0 mL of 1.5 M solution in toluene, 5.98 mmol) was added all at once. The reaction mixture was allowed to warm to room temperature over a period of 3.5 h. Methanol (1.2 mL) was added followed by water (1.2 mL) at 0° C. and the mixture was stirred at room temperature for 20 min. 1 N HCl solution was added with stirring until pH<7. The mixture was extracted with ethyl acetate (3×), washed with brine, dried over sodium sulfate, filtered, and the solvent evaporated. Purification by silica chromatography (15%-25% ethyl acetate-hexane) to yield 459 mg (91%) of the title compound as a white solid: mp 161-162° C.; 1H NMR (DMSO-d6): δ 2.67 (3H, s), 6.88 (2H, d, J=8.41 Hz), 7.59-7.65 (4H, m), 7.85 (1H,d, J=8.03 Hz), 9.78 (1H, s), 10.22 (1H, s); IR 1680 cm−1; MS (ESI) m/z 211 (M−H)−.

Workup

  1. stirringwith stirring until pH<7
  2. extractionThe mixture was extracted with ethyl acetate (3×)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customPurification by silica chromatography (15%-25% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-81b91d9438174aed8e5dce246591d9cf
Source dataset
uspto-grants-2007_10
Patent number
US07279600B2

Reaction notes

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