1,4-Dihydroxy-2-naphthoic acid → 1-Hydroxy-4-(beta-bromoethoxy)-2-naphthoic acid

HRID 848576Notes

Reaction equation

HRID 848576 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].[Br:16][CH2:17][CH2:18]O>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:18][CH2:17][Br:16])=[CH:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

3

Reactant 2

HCID 6711,4-Dihydroxy-2-naphthoic acidHCID 108982-Bromoethanol

Product 1

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

Conditions

Temperature
90 °C

Procedure

60 g (0.3 mol) of 1,4-dihydroxy-2-naphthoic acid was added to 150 ml of 2-bromoethanol and, under heating at 90° C. with stirring, hydrogen chloride gas was bubbled into the mixture during a reaction period of 2 hours. The mixture was then cooled to from 10° to 20° C. and the crystals precipitated were collected by filtration to obtain 47.4 g (50% yield) of 1-hydroxy-4-(β-bromoethoxy)-2-naphthoic acid.

Workup

  1. customhydrogen chloride gas was bubbled into the mixture during a reaction period of 2 hours
  2. temperatureThe mixture was then cooled to from 10° to 20° C.
  3. customthe crystals precipitated
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-513037ecc1254dad9b895a2c7a80966c
Source dataset
uspto-grants-1981_10
Patent number
US04296199

Reaction notes

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