Sodium borohydride → (2-{[4-(Hydroxymethyl)phenyl]methyl}phenyl)methanol

HRID 648129Notes

Reaction equation

HRID 648129 reaction equation
[BH4-].[Na+].C([O:5][C:6]([C:8]1[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=1[CH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1)=O)C.[Cl-].[Al+3].[Cl-].[Cl-]>COCCOCCOC>[OH:5][CH2:6][C:8]1[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=1[CH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) ChlorideHCID 20484759HCID 20484759, compound

Product 1

HCID 54116134(2-{[4-(Hydroxymethyl)phenyl]methyl}phenyl)methanolYield 84.3%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent3×

Procedure

Sodium borohydride (7.6 g) was added to 200 ml of diglyme, and with stirring at room temperature, a solution of 39.3 g of 4-(2-ethoxycarbonylbenzyl)benzaldehyde in 50 ml of diglyme was added dropwise over the course of 25 minutes. Subsequently, a solution of 9.33 g of anhydrous aluminum chloride in 50 ml of diglyme was added dropwise over the course of 15 minutes. The mixture was stirred at room temperature for 2 hours, and then at 45° to 50° C. for 1 hour. The reaction mixture was poured into about 3 liters of ice water, and stirred. The precipitated crystals were collected by filtration, washed with water, dried, and recrystallized from benzene to afford 28.2 g of 4-(2-hydroxymethylbenzyl)benzyl alcohol as colorless needle-like crystals having a melting point of 101.5° to 102° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. stirringstirred
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized from benzene

Sources & evidence

ORD record
ord-1f14093e293b4210aa55de8961b732d8
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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