Sodium borohydride → 1,8-Dibutoxyanthracene

HRID 1440950Notes

Reaction equation

HRID 1440950 reaction equation
[CH2:1]([O:5][C:6]1[C:19]2[C:18](=O)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[O:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11](=O)[C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>C(O)(C)C>[CH2:22]([O:21][C:16]1[C:17]2[C:12](=[CH:11][C:10]3[C:19]([CH:18]=2)=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH:7]=[CH:8][CH:9]=3)[CH:13]=[CH:14][CH:15]=1)[CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 158559451,8-Dibutoxyanthraquinone

Product 1

HCID 224204921,8-DibutoxyanthraceneYield 85.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1,8-dibutoxyanthraquinone (38 g, 0.108 mol), sodium borohydride (20.5 g, 0.54 mol), and 800 mL of isopropanol was stirred at reflux for 18 hours, and then cooled. The excess borohydride was destroyed by the cautious addition of 20% aqueous HCl, and the product was extracted into dichloromethane. The extract was washed with water and dried with MgSO4, and the solvent was removed. The residue was recrystallized from ligroin to produce 29.8 grams of 1,8-dibutoxyanthracene, which has the structural formula: ##STR49##

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. customThe excess borohydride was destroyed by the cautious addition of 20% aqueous HCl
  4. extractionthe product was extracted into dichloromethane
  5. washThe extract was washed with water
  6. dry with materialdried with MgSO4
  7. customthe solvent was removed
  8. customThe residue was recrystallized from ligroin

Sources & evidence

ORD record
ord-5328a8e7ae594399b1201ef02b82a33c
Source dataset
uspto-grants-1996_03
Patent number
US05501821

Reaction notes

Loading…