4-Hydroxybenzoic Acid → 4-(Dodecyloxy)benzoic acid

HRID 2380175Notes

Reaction equation

HRID 2380175 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].Cl>C(O)C>[CH2:25]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 89191-BromododecaneHCID 14798Sodium Hydroxide2×

Product 1

HCID 753304-(Dodecyloxy)benzoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.17 g of sodium hydroxide was dissolved in 100 ml of ethyl alcohol. Then, 5.03 g of para-hydroxy benzoic acid and 12.2 ml of 1-bromododecane were added to the solution and refluxed for 15 hours. 50 ml of 10% aqueous sodium hydroxide solution was added and refluxed for another 2 hours. After cooling, concentrated HCl was dropped into the solution until it was acidic. Filtration and recrystallization from ethyl alcohol gave 7.66 g of pure product (yield 70%).

Workup

  1. temperaturerefluxed for 15 hours
  2. temperaturerefluxed for another 2 hours
  3. temperatureAfter cooling
  4. filtrationFiltration and recrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-2461da914adc45f6b1499794c501d4ef
Source dataset
uspto-grants-1994_11
Patent number
US05366656

Reaction notes

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