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

HRID 2380174Notes

Reaction equation

HRID 2380174 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][CH3:23].Cl>C(O)C>[CH2:14]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 81731-BromodecaneHCID 14798Sodium Hydroxide2×

Product 1

HCID 1385274-(Decyloxy)benzoic acidYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.11 g of sodium hydroxide was dissolved in 50 ml of ethyl alcohol and to the solution were added 2.6 g of para-hydroxy benzoic acid and 5.8 ml of 1-bromodecane. After the mixture was refluxed for 15 hours, 25 ml of 10% aqueous sodium hydroxide solution was added and refluxed for another two hours. After cooling, concentrated HCl was dropped into the solution until it was acidic. Filtration and recrystallization from ethyl alcohol gave 3.8 g of pure product (yield 73%).

Workup

  1. temperatureAfter the mixture was refluxed for 15 hours
  2. temperaturerefluxed for another two hours
  3. temperatureAfter cooling
  4. filtrationFiltration and recrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-dddbc2c6e8a94760b437f73afe49922a
Source dataset
uspto-grants-1994_11
Patent number
US05366656

Reaction notes

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