4-Hydroxybenzoic Acid → HCID 14989397, compound

HRID 429391Notes

Reaction equation

HRID 429391 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:13](Br)[C:14]#[CH:15]>C(O)(C)C>[CH2:15]([O:7][C:6]([C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1)=[O:8])[C:14]#[CH:13]

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 7842Propargyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 14989397HCID 14989397, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

p-Hydroxybenzoic acid (0.724 mole) and sodium hydroxide (0.724 mole) were dissolved in 50% isopropyl alcohol (400 ml). Propargyl bromide (0.724 mole) was added and the solution was heated to reflux for 6 hours. The solution was then cooled and the isopropyl alcohol was removed under vacuum. The residue was taken up in methylene chloride (200 ml), washed with water (200 ml), aturated sodium bicarbonate, saline and dried over magnesium sulfate. Removal of the solvent yielded crude product, which was recrystallized, from CCI4 to give pure propargylparaben. (62.9% yield) m.p. 107-108° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 6 hours
  3. temperatureThe solution was then cooled
  4. customthe isopropyl alcohol was removed under vacuum
  5. washwashed with water (200 ml), aturated sodium bicarbonate, saline
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent
  8. customyielded crude product, which
  9. customwas recrystallized, from CCI4

Sources & evidence

ORD record
ord-07aeed9b8f09430ca104888832266a3e
Source dataset
uspto-grants-2001_11
Patent number
US06316500B1

Reaction notes

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