4'-Chlorobiphenyl-2-carbaldehyde → 2-(4-Chlorophenyl)benzyl alcohol

HRID 2406226Notes

Reaction equation

HRID 2406226 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:14]=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][OH:15])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 13936894'-Chlorobiphenyl-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 13927802-(4-Chlorophenyl)benzyl alcoholYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4′-Chloro-biphenyl-2-carbaldehyde (6.50 g, 30.0 mmol) was dissolved in CH2Cl2 (75 mL) and methanol (75 mL). The solution was cooled to 0° C. in an ice bath, and then sodium borohydride (1.36 g, 36.0 mmol) was added slowly portionwise. The reaction was allowed to warm gradually to room temperature and stir for 16 hours. The reaction was quenched by addition of 2M NaOH, and the organics were extracted with CH2Cl2 (3×75 mL). The combined organic layers were dried over MgSO4 and concentrated to afford (4′-chloro-biphenyl-2-yl)-methanol (6.42 g, 98% yield), which was carried on to the next step without further purification. MS (ES1) m/e (M−H)−: 217.4

Workup

  1. temperatureto warm gradually to room temperature
  2. customThe reaction was quenched by addition of 2M NaOH
  3. extractionthe organics were extracted with CH2Cl2 (3×75 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8c3cae65b60f45bba87f495ea27a582c
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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