Hydrogen Bromide → HCID 22133418, compound

HRID 326397Notes

Reaction equation

HRID 326397 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[O:17]C)[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[OH-].[Na+].Cl>C(O)(=O)C>[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[OH:17])[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18626122HCID 18626122, compound

Product 1

HCID 22133418HCID 22133418, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-phenoxy-4-methoxybenzoic acid (17.0 g, 0.07 mole), a 48 weight percent aqueous solution of HBr (165 ml, 1.39 mole) and 350 ml of glacial acetic acid was added to a 1-liter, one-necked, round-bottom flask equipped with a reflux condenser, nitrogen inlet adapter and a polytetrafluoroethylene-coated magnetic stir bar. The solution was heated under nitrogen and refluxed for 16 hours. While still hot, the flask was transferred to a rotary evaporator and the volatiles were removed leaving a salmon-colored solid which was added to 200 ml of 1.25N NaOH solution (0.25 mole). Most of the solid dissolved. The insoluble portion was filtered off. The remaining aqueous base solution was added dropwise to a stirred aqueous HCl solution (0.25 mole in 400 ml deionized water) resulting in the precipitation of a salmon-colored solid. The solid was washed in 300 ml of deionized water for 1 hour, filtered, dried at room temperature overnight, and dried under vacuum at 100° C. for 1 hour yielding 3-phenoxy-4-hydroxybenzoic acid.

Workup

  1. customone-necked, round-bottom flask equipped with a reflux condenser, nitrogen inlet adapter and a polytetrafluoroethylene-coated magnetic stir bar
  2. temperatureThe solution was heated under nitrogen
  3. temperaturerefluxed for 16 hours
  4. customWhile still hot, the flask was transferred to a rotary evaporator
  5. customthe volatiles were removed
  6. customleaving a salmon-colored solid which
  7. dissolutionMost of the solid dissolved
  8. filtrationThe insoluble portion was filtered off
  9. customresulting in the precipitation of a salmon-colored solid
  10. washThe solid was washed in 300 ml of deionized water for 1 hour
  11. filtrationfiltered
  12. customdried at room temperature overnight
  13. customdried under vacuum at 100° C. for 1 hour

Sources & evidence

ORD record
ord-c41417ec12864a7ba1a5a0608ae0eb5f
Source dataset
uspto-grants-1993_12
Patent number
US05268443

Reaction notes

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