Hydrochloric Acid → 1-Hydroxy-4-(beta-bromoethoxy)-2-naphthoic acid

HRID 2166910Notes

Reaction equation

HRID 2166910 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]=1[C:13]([OH:15])=[O:14].Cl.[Br:17][CH2:18][CH2:19]O>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:19][CH2:18][Br:17])=[CH:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6711,4-Dihydroxy-2-naphthoic acidHCID 108982-Bromoethanol

Product 1

HCID 204973241-Hydroxy-4-(beta-bromoethoxy)-2-naphthoic acidYield 50%

Procedure

To 150 ml of 2-bromoethanol, 60 g (0.3 mol) of 1,4-dihydroxy-2-naphthoic acid was added, and the reaction was carried out at 90° C. with stirring for 2 hours while introducing hydrogen chloride gas. After being cooled (10°-20° C.), precipitated crystals were separated by filtration to obtain 47.4 g (50% yield) of 1-hydroxy-4-(β-bromoethoxy)-2-naphthoic acid.

Workup

  1. customwas carried out at 90° C.
  2. temperatureAfter being cooled (10°-20° C.)
  3. customprecipitated crystals
  4. customwere separated by filtration

Sources & evidence

ORD record
ord-8568b6f3195545d4a270de978340a321
Source dataset
uspto-grants-1983_06
Patent number
US04390618

Reaction notes

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