2-Chloroethanol → 2-(2-Amino-5-nitrophenoxy)ethan-1-ol

HRID 892352Notes

Reaction equation

HRID 892352 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].Cl[CH2:13][CH2:14][OH:15].[OH-].[Na+]>CS(C)=O>[OH:15][CH2:14][CH2:13][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 14798Sodium HydroxideHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 125379162-(2-Amino-5-nitrophenoxy)ethan-1-olYield 58.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-amino-5-nitrophenol (1, 30 g), 2-chloroethanol (24.2 g) and sodium hydroxide (powdered, 12 g) in DMSO (100 ml) was stirred for 2.5 h at 110° C. The mixture was poured onto crushed ice (200 g) and the dark yellow precipitate was filtered, washed with H2O three times. Recrystallization from ethanol gave 22.4 g (58%) of 2: mp 140°-142° C.; MS m/e 198 (M+).

Workup

  1. additionThe mixture was poured
  2. filtrationthe dark yellow precipitate was filtered
  3. washwashed with H2O three times
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-1bb26365092a49e09ea8b18bea15482b
Source dataset
uspto-grants-1992_06
Patent number
US05118323

Reaction notes

Loading…