Boron trifluoride etherate → 5-(Dimethylamino)-2-nitrobenzenemethanol

HRID 1263060Notes

Reaction equation

HRID 1263060 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8](O)=[O:9].[BH4-].[Na+].B(F)(F)F.CCOCC>COCCOC>[CH3:1][N:2]([CH3:15])[C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 127157935-(Dimethylamino)-2-nitrobenzoic acid

Product 1

HCID 144593355-(Dimethylamino)-2-nitrobenzenemethanol

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 189 g of 5-dimethylamino-2-nitrobenzoic acid in 1.5 l of 1,2-dimethoxyethane was treated with 52 g of sodium borohydride and then dropwise at 10° with a solution of 225 ml of boron trifluoride etherate in 500 ml of 1,2-dimethoxyethane. The mixture was then stirred at room temperature for 1 hour, cautiously poured into ice/water and the crude product was filtered. Recrystallization from ethyl acetate/hexane gave pure 5-dimethylamino-2-nitrobenzyl alcohol, m.p. 138°-139°.

Workup

  1. customdropwise at 10°
  2. filtrationthe crude product was filtered
  3. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-05452fb76a414aa3bb6a27c3fbcefead
Source dataset
uspto-grants-1984_06
Patent number
US04455311

Reaction notes

Loading…