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

HRID 2380177

Reaction equation

HRID 2380177 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][CH2:27][CH3:28].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][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 127421-BromononaneHCID 14798Sodium Hydroxide2×HCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 36202634'-(Nonyloxy)[1,1'-biphenyl]-4-carboxylic acidYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.12 g of sodium hydroxide was dissolved in 100 ml of ethyl alcohol. Then, 2.0 g of 4-(4'-hydroxyphenyl) benzoic acid and 2.3 ml of 1-bromononane were added to the solution and refluxed for 19 hours. 50 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. After filtration and recrystallization from ethyl alcohol gave 2.18 g of pure product (yield 69%).

Workup

  1. temperaturerefluxed for 19 hours
  2. temperaturerefluxed for another two hours
  3. temperatureAfter cooling
  4. filtrationAfter filtration and recrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-2326ebe5abc84c5283baac9b3faab9cc
Source dataset
uspto-grants-1994_11
Patent number
US05366656

Linked notes

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