Sodium borohydride → Methyl 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carboxylate

HRID 1186029Notes

Reaction equation

HRID 1186029 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)=[O:4]>CO>[OH:4][CH2:3][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 4325150Methyl 2-(4-formylphenyl)benzoate

Product 1

HCID 15380881Methyl 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carboxylateYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (111 mg) was added to the compound (400 mg) prepared in Example 4 in methanol solution (10 mL) and stirred for 1 hour at room temperature. The reaction mixture was concentrated and extracted with 1 mol/L hydrochloric acid and ethyl acetate. The organic layer was washed with saturated sodium and dried by anhydrous sodium sulfate, and then concentrated to obtain the titled compound (400 mg) having the following physical data.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with 1 mol/L hydrochloric acid and ethyl acetate
  3. washThe organic layer was washed with saturated sodium
  4. dry with materialdried by anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ab82958328ea41619d1ccd1c77d93663
Source dataset
uspto-grants-2014_03
Patent number
US08673889B2

Reaction notes

Loading…