Chloroform → 4-Methoxybenzhydryl alcohol

HRID 369920

Reaction equation

HRID 369920 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.C(Cl)(Cl)Cl>CO>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 691464-MethoxybenzophenoneHCID 4311764Sodium borohydride2×

Product 1

HCID 953754-Methoxybenzhydryl alcoholYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Solid NaBH4 (2.55 g, 0.067 mol) was added portion-wise to a solution of p-methoxybenzophenone (25.14 g, 0.118 mol) in MeOH (150 mL) at room temperature over 10 min. After the exothermic reaction had subsided, the reaction mixture was stirred at room temperature for 2 h. TLC (SiO2, CHCl3) indicated incomplete reaction; therefore, additional NaBH4 (2.55 g) was added and the reaction mixture was stirred at room temperature an additional 2 h. The MeOH was evaporated and the residue partitioned between water (100 mL) and CH2Cl2 (100 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (200 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated to give the alcohol (25.24 g, 99%) as a white solid: m.p. 66-67° C. The structure was confirmed by 1H--NMR in CDCl3.

Workup

  1. customAfter the exothermic reaction
  2. customreaction
  3. stirringthe reaction mixture was stirred at room temperature an additional 2 h
  4. customThe MeOH was evaporated
  5. customthe residue partitioned between water (100 mL) and CH2Cl2 (100 mL)
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with CH2Cl2 (200 mL)
  8. dry with materialThe combined organic layers were dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-b238aa7ed36048e395c3d404301797b7
Source dataset
uspto-grants-2000_10
Patent number
US06140137

Linked notes

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