Hydrochloric Acid → 4'-(Octyloxy)-[1,1'-biphenyl]-4-carboxylic acid

HRID 2380176Notes

Reaction equation

HRID 2380176 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].Cl>C(O)C>[CH2:20]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81401-BromooctaneHCID 14798Sodium Hydroxide2×HCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 28025564'-(Octyloxy)-[1,1'-biphenyl]-4-carboxylic acidYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.15 g of sodium hydroxide was dissolved in 100 ml of ethyl alcohol. Then, 2.0 g of 4-(4'-hydroxyphenyl) benzoic acid and 2.45 ml of 1-bromooctane were added to the solution and refluxed for 16 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 1.95 g of pure product (yield 64%).

Workup

  1. temperaturerefluxed for 16 hours
  2. temperaturerefluxed for another 2 hours
  3. temperatureAfter cooling
  4. filtrationFiltration and recrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-cd9abff4c6bb41ccbe748f0208f1a667
Source dataset
uspto-grants-1994_11
Patent number
US05366656

Reaction notes

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