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

HRID 848575Notes

Reaction equation

HRID 848575 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][CH:17]([CH2:20][Br:21])[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][CH:17]([Br:16])[CH2:20][Br:21])=[CH:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

3

Reactant 2

HCID 6711,4-Dihydroxy-2-naphthoic acidHCID 72812,3-Dibromo-1-propanol

Product 1

HCID 205655531-Hydroxy-4-(beta,gamma-dibromopropyloxy)-2-naphthoic acidYield 35%

Conditions

Temperature
90 °C

Procedure

60 g (0.3 mol) of 1,4-dihydroxy-2-naphthoic acid was added to 150 ml of 2,3-dibromopropanol and, under heating at 90° C. with stirring, hydrogen chloride gas was bubbled in the mixture during a reaction period of 2 hours. The mixture was cooled to 10° to 20° C. and the crystals precipitated were collected by filteration to obtain 42.4 g (35% yield) of 1-hydroxy-4-(β,γ-dibromopropyloxy)-2-naphthoic acid.

Workup

  1. customhydrogen chloride gas was bubbled in the mixture during a reaction period of 2 hours
  2. temperatureThe mixture was cooled to 10° to 20° C.
  3. customthe crystals precipitated
  4. customwere collected by filteration

Sources & evidence

ORD record
ord-871727e329864f6f9d3d0279cb7bc2d2
Source dataset
uspto-grants-1981_10
Patent number
US04296200

Reaction notes

Loading…