Hydrochloric Acid → 3'-Chloro-4'-octyloxy-4-biphenylcarboxylic acid

HRID 1033699

Reaction equation

HRID 1033699 reaction equation
[Cl:1]N(Cl)S(C1C=CC(C)=CC=1)(=O)=O.Cl.[CH2:15]([O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(O)(=O)C>[Cl:1][C:25]1[CH:26]=[C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[CH:32][CH:31]=2)[CH:28]=[CH:29][C:24]=1[O:23][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68056Dichloramine-T2×HCID 28025564'-(Octyloxy)-[1,1'-biphenyl]-4-carboxylic acid

Product 1

HCID 147941813'-Chloro-4'-octyloxy-4-biphenylcarboxylic acidYield 128.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

N,N-dichloro-p-toluenesulfonamide (hereinafter abbreviated to "dichloramine T") (7.5 g, 0.032 mol) was dissolved in acetic acid (100 ml), followed by adding to the solution, hydrochloric acid (0.4 ml), dropwise adding to the acetic acid solution of dichloramine T, a solution of 4'-octyloxy-4-biphenylcarboxylic acid (20 g, 0.063 mol) dissolved in acetic acid (100 ml), refluxing the mixture, allowing it to stand overnight, distilling off acetic acid and filtering off deposited crystals to obtain 3'-chloro-4'-octyloxy-4-biphenylcarboxylic acid (14.8 g) (C-Sc 146° C., Sc '-N' 224° C. and N'-I 232° C.).

Workup

  1. temperaturerefluxing the mixture
  2. distillationdistilling off acetic acid
  3. filtrationfiltering off

Sources & evidence

ORD record
ord-efebf27abd834d94a66ef657ccdc98b9
Source dataset
uspto-grants-1994_05
Patent number
US05312564

Linked notes

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