4-Hydroxybenzoic Acid → 4-Butoxybenzoic acid

HRID 466501Notes

Reaction equation

HRID 466501 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH3:5].[OH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.[OH-].[Na+].O>C(O)C>[CH2:2]([O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 962WaterHCID 8002Butyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 729714-Butoxybenzoic acidYield 65.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-Bromobutane (22.6 g, 0.165 mol) was added dropwise at room temperature to a stirred mixture of 4-hydroxybenzoic acid (15.0 g, 0.11 mol) in ethanol (60 ml) and sodium hydroxide (10.60 g) in the minimum amount of water. The stirred mixture was heated under reflux overnight (tlc analysis revealed a complete reaction), and then the ethanol was distilled off and an equal volume of water was added. The mixture was boiled to give a solution, cooled, washed with ether and acidified with 36% hydrochloric acid. The cooled mixture was filtered, and the product was washed with water to give a colourless solid (13.9 g) which was recrystallised from ethanol to give colourless crystals.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux overnight (tlc analysis
  3. distillationwas distilled off
  4. additionan equal volume of water was added
  5. customto give a solution
  6. temperaturecooled
  7. washwashed with ether
  8. filtrationThe cooled mixture was filtered
  9. washthe product was washed with water

Sources & evidence

ORD record
ord-5ac0a0fc10a1466aa5c95ef3f0d0ee5d
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

Loading…