Sodium borohydride → Methyl 4-[3-(hydroxymethyl)phenyl]benzoate

HRID 1860015Notes

Reaction equation

HRID 1860015 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]>C(O)C>[OH:4][CH2:3][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 4321386Methyl 4-(3-formylphenyl)benzoate

Product 1

HCID 1392389Methyl 4-[3-(hydroxymethyl)phenyl]benzoateYield 71.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (132 mg) was added to a solution of methyl 3′-formylbiphenyl-4-carboxylate (720 mg), which is the product of Reference example 14(a), in ethanol (50 ml) at ambient temperature. The mixture was stirred under an atmosphere of nitrogen for 50 minutes. The reaction mixture was quenched with 50% acetic acid and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to afford the desired compound (522 mg) as colorless crystals.

Workup

  1. customat ambient temperature
  2. customThe reaction mixture was quenched with 50% acetic acid
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe layers were separated
  6. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-613ebbfcf39a474f9a3effd1a7a8d645
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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