Hydrochloric Acid → 4-Pentyl-4'-biphenylcarboxylic Acid

HRID 328310Notes

Reaction equation

HRID 328310 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:20])C)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].BrBr.BrO.S(=O)(O)[O-:26].[Na+].Cl>[OH-].[Na+].O.O1CCOCC1>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([OH:20])=[O:26])=[CH:16][CH:17]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24408BromineHCID 83547Hypobromous acidHCID 52444161-(4'-Pentyl-1,1'-biphenyl-4-yl)ethanoneHCID 23665763Sodium Bisulfite

Product 1

HCID 20633354-Pentyl-4'-biphenylcarboxylic AcidYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent2×

Procedure

883 Gram of 4'-n-pentyl-4-acetylbiphenyl was introduced into a 30 l stainless steel reactor (provided with a stirrer, a reflux condenser and a funnel for dropwise adding), added 3.75 l of p-dioxane and dissolved with stirring. On the other hand, 1.8 kg of bromine was dropwise added to and dissolved in a solution of 2 kg of sodium hydroxide dissolved in 7.5 l of water, cooled to 10°-15° C. The resulting hypobromous acid solution was maintained at about 10° C. This solution was dropwise added to the above-mentioned p-dioxane solution over 50 minutes, followed by stirring at 35°-40° C for 3 hours, allowing to stand over one night, adding 250 g of sodium bisulfite, stirring, neutralizing with 2.8 l of conc. hydrochloric acid, separating the resulting solid by filtration, water-washing, drying and recrystallizing from 6 l of acetic acid, to give 747 g of 4'-n-pentyl-4-biphenylcarboxylic acid of m.p. 177° C (smectic liquid crystal being formed) (Yield 84%).

Workup

  1. customprovided with a stirrer, a reflux condenser and a funnel
  2. additionfor dropwise adding),
  3. dissolutiondissolved
  4. temperaturecooled to 10°-15° C
  5. stirringby stirring at 35°-40° C for 3 hours
  6. waitto stand over one night
  7. stirringstirring
  8. customseparating the resulting solid
  9. filtrationby filtration, water-
  10. washwashing
  11. customdrying
  12. customrecrystallizing from 6 l of acetic acid
  13. customto give

Sources & evidence

ORD record
ord-9189d12394724e63af70ab32205fe0ba
Source dataset
uspto-grants-1977_04
Patent number
US04017416

Reaction notes

Loading…