Acetic Acid → 2-Naphthalenecarboxylic acid, 7-bromo-3-hydroxy-

HRID 1189710Notes

Reaction equation

HRID 1189710 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Br:12])=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:13]([OH:15])=[O:14])[C:3]=1[OH:16].C(O)(=O)C.[Sn].Cl>O>[Br:12][C:8]1[CH:7]=[C:6]2[C:11]([CH:2]=[C:3]([OH:16])[C:4]([C:13]([OH:15])=[O:14])=[CH:5]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 745022-Naphthalenecarboxylic acid, 4,7-dibromo-3-hydroxy-HCID 5352426Tin atom

Product 1

HCID 745032-Naphthalenecarboxylic acid, 7-bromo-3-hydroxy-Yield 96.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

In a 1 L three-necked bottle, 40 g of 4,7-dibromo-3-hydroxy-2-naphthoic acid (0.116 mol) and 500 ml of glacial acetic acid were added, and stirred to make homogenous. 18 g of tin powder (0.153 mol) and 130 ml of concentrated hydrochloric acid were then added to the mixture in order, heated to 125° C., and refluxed under heating for 12 h. 300 ml of water was added to the mixture, stirred to room temperature, filtered, and the filter cake was washed with water (200 ml*2), and dried in an oven to obtain 29.9 g of a solid with a yield of 96.5%.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 12 h
  3. stirringstirred to room temperature
  4. filtrationfiltered
  5. washthe filter cake was washed with water (200 ml*2)
  6. customdried in an oven

Sources & evidence

ORD record
ord-dc5fa820f87644598b971facd31ebc4a
Source dataset
uspto-grants-2014_03
Patent number
US08674136B2

Reaction notes

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