Ethanol → Ethyl 7-bromo-3-hydroxy-2-naphthoate

HRID 2187646Notes

Reaction equation

HRID 2187646 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([OH:15])[C:8]([C:12]([OH:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.O.C([O-])(O)=O.[Na+].[CH3:22][CH2:23]O>S(=O)(=O)(O)O>[CH2:22]([O:13][C:12]([C:8]1[C:7]([OH:15])=[CH:6][C:5]2[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=2)[CH:9]=1)=[O:14])[CH3:23]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 745032-Naphthalenecarboxylic acid, 7-bromo-3-hydroxy-HCID 516892Sodium Bicarbonate

Product 1

HCID 18476207Ethyl 7-bromo-3-hydroxy-2-naphthoateYield 85%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 81 g (0.3 mol) of 7-bromo-3-hydroxy-2-naphthoic acid in 600 ml dried EtOH and 60 ml conc. sulfuric acid was heated at reflux for 16 hours. The mixture was cooled to room temperature and treated with water (4000 ml) and neutralised with NaHCO3. The solid was separated by filtration and dried in a drying chamber afforded 75.3 g (85%) of the titled compound.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe solid was separated by filtration
  3. customdried in a drying chamber

Sources & evidence

ORD record
ord-f978a3687f9544378fc42058e1d9924b
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

Loading…